CN101522611B - 取代的苯基三氟化硫及其他类似的氟化剂 - Google Patents
取代的苯基三氟化硫及其他类似的氟化剂 Download PDFInfo
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- CN101522611B CN101522611B CN2007800360607A CN200780036060A CN101522611B CN 101522611 B CN101522611 B CN 101522611B CN 2007800360607 A CN2007800360607 A CN 2007800360607A CN 200780036060 A CN200780036060 A CN 200780036060A CN 101522611 B CN101522611 B CN 101522611B
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- Prior art keywords
- tert
- butylphenyl
- bis
- alkyl group
- trifluoride
- Prior art date
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- 239000012025 fluorinating agent Substances 0.000 title claims abstract description 109
- AECHPKVYOLOZLF-UHFFFAOYSA-N trifluoro(phenyl)-$l^{4}-sulfane Chemical class FS(F)(F)C1=CC=CC=C1 AECHPKVYOLOZLF-UHFFFAOYSA-N 0.000 title abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 157
- 238000000034 method Methods 0.000 claims abstract description 52
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 193
- 125000004432 carbon atom Chemical group C* 0.000 claims description 84
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 58
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 24
- VRTQPEYVMHATOA-UHFFFAOYSA-N (4-tert-butyl-2,6-dimethylphenyl)-trifluoro-$l^{4}-sulfane Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1S(F)(F)F VRTQPEYVMHATOA-UHFFFAOYSA-N 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 239000011593 sulfur Substances 0.000 claims description 11
- KTZZPIGQAOPDIT-UHFFFAOYSA-N (4-tert-butyl-3-chloro-2,6-dimethylphenyl)-trifluoro-$l^{4}-sulfane Chemical compound CC1=CC(C(C)(C)C)=C(Cl)C(C)=C1S(F)(F)F KTZZPIGQAOPDIT-UHFFFAOYSA-N 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- ADBHFTLCLLQJQV-UHFFFAOYSA-N [4-tert-butyl-2,6-bis(methoxymethyl)phenyl]-trifluoro-$l^{4}-sulfane Chemical compound COCC1=CC(C(C)(C)C)=CC(COC)=C1S(F)(F)F ADBHFTLCLLQJQV-UHFFFAOYSA-N 0.000 claims description 8
- LCBQDXPGEQMUPY-UHFFFAOYSA-N [4-tert-butyl-2,6-bis(propan-2-yloxymethyl)phenyl]-trifluoro-$l^{4}-sulfane Chemical compound CC(C)OCC1=CC(C(C)(C)C)=CC(COC(C)C)=C1S(F)(F)F LCBQDXPGEQMUPY-UHFFFAOYSA-N 0.000 claims description 7
- LLIONMZIJTXMOO-UHFFFAOYSA-N trifluoro-(2,4,6-trimethylphenyl)-$l^{4}-sulfane Chemical compound CC1=CC(C)=C(S(F)(F)F)C(C)=C1 LLIONMZIJTXMOO-UHFFFAOYSA-N 0.000 claims description 7
- NXIDOVWAFJTIOZ-UHFFFAOYSA-N (2,4-dimethylphenyl)-trifluoro-$l^{4}-sulfane Chemical compound CC1=CC=C(S(F)(F)F)C(C)=C1 NXIDOVWAFJTIOZ-UHFFFAOYSA-N 0.000 claims description 6
- RPVVBDLHVNYVPI-UHFFFAOYSA-N (4-tert-butyl-3,5-dichloro-2,6-dimethylphenyl)-trifluoro-$l^{4}-sulfane Chemical compound CC1=C(Cl)C(C(C)(C)C)=C(Cl)C(C)=C1S(F)(F)F RPVVBDLHVNYVPI-UHFFFAOYSA-N 0.000 claims description 6
- IZUDOPUGZYZGRX-UHFFFAOYSA-N 1-tert-butyl-4-[(4-tert-butyl-3,5-dichloro-2,6-dimethylphenyl)disulfanyl]-2,6-dichloro-3,5-dimethylbenzene Chemical compound CC1=C(Cl)C(C(C)(C)C)=C(Cl)C(C)=C1SSC1=C(C)C(Cl)=C(C(C)(C)C)C(Cl)=C1C IZUDOPUGZYZGRX-UHFFFAOYSA-N 0.000 claims description 6
- FARCQNVRJYLDHL-UHFFFAOYSA-N [2,6-bis(methoxymethyl)phenyl]-trifluoro-$l^{4}-sulfane Chemical compound COCC1=CC=CC(COC)=C1S(F)(F)F FARCQNVRJYLDHL-UHFFFAOYSA-N 0.000 claims description 6
- QKZXKHQKUHHHGL-UHFFFAOYSA-N [4-tert-butyl-2,6-bis(ethoxymethyl)phenyl]-trifluoro-$l^{4}-sulfane Chemical compound CCOCC1=CC(C(C)(C)C)=CC(COCC)=C1S(F)(F)F QKZXKHQKUHHHGL-UHFFFAOYSA-N 0.000 claims description 6
- WLSAZKAPXZFJEA-UHFFFAOYSA-N (2,5-dimethylphenyl)-trifluoro-$l^{4}-sulfane Chemical compound CC1=CC=C(C)C(S(F)(F)F)=C1 WLSAZKAPXZFJEA-UHFFFAOYSA-N 0.000 claims description 5
- BOPWFAKDRNZFFH-UHFFFAOYSA-N (4-tert-butylphenyl)-trifluoro-$l^{4}-sulfane Chemical compound CC(C)(C)C1=CC=C(S(F)(F)F)C=C1 BOPWFAKDRNZFFH-UHFFFAOYSA-N 0.000 claims description 5
- URJSMFWWDWRBRS-UHFFFAOYSA-N 1-tert-butyl-4-[(4-tert-butyl-3-chloro-2,6-dimethylphenyl)disulfanyl]-2-chloro-3,5-dimethylbenzene Chemical compound CC1=CC(C(C)(C)C)=C(Cl)C(C)=C1SSC1=C(C)C=C(C(C)(C)C)C(Cl)=C1C URJSMFWWDWRBRS-UHFFFAOYSA-N 0.000 claims description 5
- SAXWQKXTMPSEPW-UHFFFAOYSA-N [4-tert-butyl-2,6-bis(2-methylpropoxymethyl)phenyl]-trifluoro-$l^{4}-sulfane Chemical compound CC(C)COCC1=CC(C(C)(C)C)=CC(COCC(C)C)=C1S(F)(F)F SAXWQKXTMPSEPW-UHFFFAOYSA-N 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- RKJUUVQTGDGPQV-UHFFFAOYSA-N trifluoro-(4-fluorophenyl)-$l^{4}-sulfane Chemical compound FC1=CC=C(S(F)(F)F)C=C1 RKJUUVQTGDGPQV-UHFFFAOYSA-N 0.000 claims description 5
- FFIDEAICRXMXHH-UHFFFAOYSA-N (2,6-dimethylphenyl)-trifluoro-$l^{4}-sulfane Chemical compound CC1=CC=CC(C)=C1S(F)(F)F FFIDEAICRXMXHH-UHFFFAOYSA-N 0.000 claims description 4
- VMSQWEHZEPEQTJ-UHFFFAOYSA-N (4-chlorophenyl)-trifluoro-$l^{4}-sulfane Chemical compound FS(F)(F)C1=CC=C(Cl)C=C1 VMSQWEHZEPEQTJ-UHFFFAOYSA-N 0.000 claims description 4
- UCKLRNAFSVJKED-UHFFFAOYSA-N 5-tert-butyl-2-[[4-tert-butyl-2,6-bis(ethoxymethyl)phenyl]disulfanyl]-1,3-bis(ethoxymethyl)benzene Chemical compound CCOCC1=CC(C(C)(C)C)=CC(COCC)=C1SSC1=C(COCC)C=C(C(C)(C)C)C=C1COCC UCKLRNAFSVJKED-UHFFFAOYSA-N 0.000 claims description 4
- AJMHUMJGSPQBMF-UHFFFAOYSA-N 5-tert-butyl-2-[[4-tert-butyl-2,6-bis(methoxymethyl)phenyl]disulfanyl]-1,3-bis(methoxymethyl)benzene Chemical compound COCC1=CC(C(C)(C)C)=CC(COC)=C1SSC1=C(COC)C=C(C(C)(C)C)C=C1COC AJMHUMJGSPQBMF-UHFFFAOYSA-N 0.000 claims description 4
- NCBQCINXUAQLJE-UHFFFAOYSA-N 5-tert-butyl-2-[[4-tert-butyl-2,6-bis(propan-2-yloxymethyl)phenyl]disulfanyl]-1,3-bis(propan-2-yloxymethyl)benzene Chemical compound CC(C)OCC1=CC(C(C)(C)C)=CC(COC(C)C)=C1SSC1=C(COC(C)C)C=C(C(C)(C)C)C=C1COC(C)C NCBQCINXUAQLJE-UHFFFAOYSA-N 0.000 claims description 4
- DZHBEHLMGMMYAM-UHFFFAOYSA-N 5-tert-butyl-2-[[4-tert-butyl-2,6-bis[(2-methylpropan-2-yl)oxymethyl]phenyl]disulfanyl]-1,3-bis[(2-methylpropan-2-yl)oxymethyl]benzene Chemical compound CC(C)(C)OCC1=CC(C(C)(C)C)=CC(COC(C)(C)C)=C1SSC1=C(COC(C)(C)C)C=C(C(C)(C)C)C=C1COC(C)(C)C DZHBEHLMGMMYAM-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- HDYCFECPUZMCGA-UHFFFAOYSA-N trifluoro-[2,4,6-tri(propan-2-yl)phenyl]-$l^{4}-sulfane Chemical compound CC(C)C1=CC(C(C)C)=C(S(F)(F)F)C(C(C)C)=C1 HDYCFECPUZMCGA-UHFFFAOYSA-N 0.000 claims description 4
- AXULARCHGARMEW-UHFFFAOYSA-N (4-chloro-3-methylphenyl)-trifluoro-$l^{4}-sulfane Chemical compound CC1=CC(S(F)(F)F)=CC=C1Cl AXULARCHGARMEW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- WPBPJEACFSUNOP-UHFFFAOYSA-N 5-tert-butyl-2-[[4-tert-butyl-2,6-bis(2-methylpropoxymethyl)phenyl]disulfanyl]-1,3-bis(2-methylpropoxymethyl)benzene Chemical compound CC(C)COCC1=CC(C(C)(C)C)=CC(COCC(C)C)=C1SSC1=C(COCC(C)C)C=C(C(C)(C)C)C=C1COCC(C)C WPBPJEACFSUNOP-UHFFFAOYSA-N 0.000 claims description 3
- QFIXCRWZABGVNF-UHFFFAOYSA-N [4-tert-butyl-2,6-bis[(2-methylpropan-2-yl)oxymethyl]phenyl]-trifluoro-$l^{4}-sulfane Chemical compound CC(C)(C)OCC1=CC(C(C)(C)C)=CC(COC(C)(C)C)=C1S(F)(F)F QFIXCRWZABGVNF-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000006229 isopropoxyethyl group Chemical group [H]C([H])([H])C([H])(OC([H])([H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 2
- CHVBZKQBISCERD-UHFFFAOYSA-N 2-[[2,6-bis(methoxymethyl)phenyl]disulfanyl]-1,3-bis(methoxymethyl)benzene Chemical compound COCC1=CC=CC(COC)=C1SSC1=C(COC)C=CC=C1COC CHVBZKQBISCERD-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 36
- 239000000758 substrate Substances 0.000 abstract description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 90
- 230000015572 biosynthetic process Effects 0.000 description 83
- 238000003786 synthesis reaction Methods 0.000 description 80
- 229910052731 fluorine Inorganic materials 0.000 description 53
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 52
- 239000011737 fluorine Substances 0.000 description 52
- 238000006243 chemical reaction Methods 0.000 description 43
- 239000000203 mixture Substances 0.000 description 43
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- 238000005160 1H NMR spectroscopy Methods 0.000 description 33
- -1 Selenium compound selenium tetrafluoride Chemical class 0.000 description 32
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Substances CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 32
- 230000003595 spectral effect Effects 0.000 description 28
- 238000004293 19F NMR spectroscopy Methods 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 22
- 239000000463 material Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 20
- 229920002313 fluoropolymer Polymers 0.000 description 19
- 239000004811 fluoropolymer Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 18
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 238000000354 decomposition reaction Methods 0.000 description 14
- 239000000543 intermediate Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 229910052801 chlorine Inorganic materials 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
- 238000003682 fluorination reaction Methods 0.000 description 11
- 230000007062 hydrolysis Effects 0.000 description 11
- 238000006460 hydrolysis reaction Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- MFNGAMRVCCZXCD-UHFFFAOYSA-N 5-tert-butyl-2-[(4-tert-butyl-2,6-dimethylphenyl)disulfanyl]-1,3-dimethylbenzene Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1SSC1=C(C)C=C(C(C)(C)C)C=C1C MFNGAMRVCCZXCD-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 7
- 238000006140 methanolysis reaction Methods 0.000 description 7
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- 238000001308 synthesis method Methods 0.000 description 7
- 238000010189 synthetic method Methods 0.000 description 7
- BKMPHOHXSLNPRQ-UHFFFAOYSA-N 2-bromo-1,3-bis(methoxymethyl)benzene Chemical compound COCC1=CC=CC(COC)=C1Br BKMPHOHXSLNPRQ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 150000002019 disulfides Chemical class 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- OJKKNBBEBCFAGF-UHFFFAOYSA-N (4-tert-butyl-3-chloro-2,4-dimethylcyclohexa-1,5-dien-1-yl)-trifluoro-$l^{4}-sulfane Chemical compound CC1=C(S(F)(F)F)C=CC(C)(C(C)(C)C)C1Cl OJKKNBBEBCFAGF-UHFFFAOYSA-N 0.000 description 5
- 0 C*c(cc(*)cc1*)c1S Chemical compound C*c(cc(*)cc1*)c1S 0.000 description 5
- PSCXEUSWZWRCMQ-UHFFFAOYSA-N F[S](F)F Chemical compound F[S](F)F PSCXEUSWZWRCMQ-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- KWVVTSALYXIJSS-UHFFFAOYSA-L silver(ii) fluoride Chemical compound [F-].[F-].[Ag+2] KWVVTSALYXIJSS-UHFFFAOYSA-L 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000011698 potassium fluoride Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 3
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 3
- HZWYWYSLHBTTRW-UHFFFAOYSA-N 4-tert-butyl-2,6-dimethylbenzenesulfonyl chloride Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1S(Cl)(=O)=O HZWYWYSLHBTTRW-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000012776 electronic material Substances 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000003270 potassium fluoride Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000779 smoke Substances 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000002076 thermal analysis method Methods 0.000 description 3
- LSJNBGSOIVSBBR-UHFFFAOYSA-N thionyl fluoride Chemical class FS(F)=O LSJNBGSOIVSBBR-UHFFFAOYSA-N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 125000006230 (methoxyethoxy)ethanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- AOMJIUUKFCINIG-UHFFFAOYSA-N 1,3,5-trimethyl-2-[(2,4,6-trimethylphenyl)disulfanyl]benzene Chemical compound CC1=CC(C)=CC(C)=C1SSC1=C(C)C=C(C)C=C1C AOMJIUUKFCINIG-UHFFFAOYSA-N 0.000 description 2
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- 238000010908 decantation Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
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- 238000001914 filtration Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
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- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
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- 229910052749 magnesium Inorganic materials 0.000 description 2
- IXVOVVPVAXAFIV-UHFFFAOYSA-N o-methyl benzenecarbothioate Chemical compound COC(=S)C1=CC=CC=C1 IXVOVVPVAXAFIV-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000000276 potassium ferrocyanide Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- 238000004809 thin layer chromatography Methods 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
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- DJNTWAOKDVWVFA-UHFFFAOYSA-N (4-tert-butyl-2,4-dimethylcyclohexa-1,5-dien-1-yl)-trifluoro-lambda4-sulfane Chemical compound CC1=C(S(F)(F)F)C=CC(C)(C(C)(C)C)C1 DJNTWAOKDVWVFA-UHFFFAOYSA-N 0.000 description 1
- GLBJEBQCIZKKHA-UHFFFAOYSA-N 1,1-difluoro-3-methylbutane Chemical compound CC(C)CC(F)F GLBJEBQCIZKKHA-UHFFFAOYSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
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- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
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- AJUVPKHTGUJCEW-UHFFFAOYSA-N 1-heptyl-4-(trifluoromethyl)benzene Chemical compound CCCCCCCC1=CC=C(C(F)(F)F)C=C1 AJUVPKHTGUJCEW-UHFFFAOYSA-N 0.000 description 1
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- MGDCBOKBTJIJBT-UHFFFAOYSA-N 2,2-difluoro-1,3-dimethylimidazolidine Chemical compound CN1CCN(C)C1(F)F MGDCBOKBTJIJBT-UHFFFAOYSA-N 0.000 description 1
- LUGHQYFCYGQCLK-UHFFFAOYSA-N 2-[(2,5-dimethylphenyl)disulfanyl]-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(SSC=2C(=CC=C(C)C=2)C)=C1 LUGHQYFCYGQCLK-UHFFFAOYSA-N 0.000 description 1
- LKOHGPFWLCKZQQ-UHFFFAOYSA-N 2-[(2,6-dimethylphenyl)disulfanyl]-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1SSC1=C(C)C=CC=C1C LKOHGPFWLCKZQQ-UHFFFAOYSA-N 0.000 description 1
- DUSFWKQNQGLNDN-UHFFFAOYSA-N 2-bromo-5-tert-butyl-1,3-bis(2-methylpropoxymethyl)benzene Chemical compound CC(C)COCC1=CC(C(C)(C)C)=CC(COCC(C)C)=C1Br DUSFWKQNQGLNDN-UHFFFAOYSA-N 0.000 description 1
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- NSHIJHRRMBNYOD-UHFFFAOYSA-N 2-bromo-5-tert-butyl-1,3-bis[(2-methylpropan-2-yl)oxymethyl]benzene Chemical compound CC(C)(C)OCC1=CC(C(C)(C)C)=CC(COC(C)(C)C)=C1Br NSHIJHRRMBNYOD-UHFFFAOYSA-N 0.000 description 1
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- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
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- VSUKEWPHURLYTK-UHFFFAOYSA-N 4-heptylbenzoic acid Chemical compound CCCCCCCC1=CC=C(C(O)=O)C=C1 VSUKEWPHURLYTK-UHFFFAOYSA-N 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
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- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
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- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- JDZLOJYSBBLXQD-UHFFFAOYSA-N difluoromethylbenzene Chemical compound FC(F)C1=CC=CC=C1 JDZLOJYSBBLXQD-UHFFFAOYSA-N 0.000 description 1
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 1
- 150000004252 dithioacetals Chemical class 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 150000002023 dithiocarboxylic acids Chemical class 0.000 description 1
- 125000005022 dithioester group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
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- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000004175 fluorobenzyl group Chemical group 0.000 description 1
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 1
- 230000005714 functional activity Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000013056 hazardous product Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- IHPDTPWNFBQHEB-UHFFFAOYSA-N hydrobenzoin Chemical compound C=1C=CC=CC=1C(O)C(O)C1=CC=CC=C1 IHPDTPWNFBQHEB-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- DMNYFEWFSFTYEL-UHFFFAOYSA-N pentafluoro(phenyl)-$l^{6}-sulfane Chemical compound FS(F)(F)(F)(F)C1=CC=CC=C1 DMNYFEWFSFTYEL-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940065287 selenium compound Drugs 0.000 description 1
- PMOBWAXBGUSOPS-UHFFFAOYSA-N selenium tetrafluoride Chemical compound F[Se](F)(F)F PMOBWAXBGUSOPS-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003450 sulfenic acids Chemical class 0.000 description 1
- WSANLGASBHUYGD-UHFFFAOYSA-N sulfidophosphanium Chemical class S=[PH3] WSANLGASBHUYGD-UHFFFAOYSA-N 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000005323 thioketone group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- GQHWSLKNULCZGI-UHFFFAOYSA-N trifluoromethoxybenzene Chemical compound FC(F)(F)OC1=CC=CC=C1 GQHWSLKNULCZGI-UHFFFAOYSA-N 0.000 description 1
- GETTZEONDQJALK-UHFFFAOYSA-N trifluorotoluene Substances FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- 239000012989 trithiocarbonate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
- C07C323/09—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/18—Preparation of halogenated hydrocarbons by replacement by halogens of oxygen atoms of carbonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B39/00—Halogenation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
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- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
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- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
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- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
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- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
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- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/19—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to acyclic carbon atoms of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
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- C—CHEMISTRY; METALLURGY
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- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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Abstract
Description
Claims (44)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US11/494,983 | 2006-07-28 | ||
US11/494,983 US7265247B1 (en) | 2006-07-28 | 2006-07-28 | Substituted phenylsulfur trifluoride and other like fluorinating agents |
PCT/US2007/074359 WO2008014345A2 (en) | 2006-07-28 | 2007-07-25 | Substituted phenylsulfur trifluoride and other like fluorinating agents |
Publications (2)
Publication Number | Publication Date |
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CN101522611A CN101522611A (zh) | 2009-09-02 |
CN101522611B true CN101522611B (zh) | 2013-07-17 |
Family
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CN2007800360607A Active CN101522611B (zh) | 2006-07-28 | 2007-07-25 | 取代的苯基三氟化硫及其他类似的氟化剂 |
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US (6) | US7265247B1 (zh) |
EP (1) | EP2046735B1 (zh) |
JP (2) | JP4531852B2 (zh) |
KR (1) | KR100949654B1 (zh) |
CN (1) | CN101522611B (zh) |
CA (1) | CA2658364C (zh) |
RU (1) | RU2451011C2 (zh) |
TW (1) | TWI325857B (zh) |
UA (1) | UA96301C2 (zh) |
WO (2) | WO2008013550A1 (zh) |
Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
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US7265247B1 (en) | 2006-07-28 | 2007-09-04 | Im&T Research, Inc. | Substituted phenylsulfur trifluoride and other like fluorinating agents |
US8399720B2 (en) * | 2007-03-23 | 2013-03-19 | Ube Industries, Ltd. | Methods for producing fluorinated phenylsulfur pentafluorides |
CA2857831C (en) | 2007-03-23 | 2017-01-03 | Ube Industries, Ltd. | Process for producing arylsulfur pentafluorides |
US8030516B2 (en) * | 2007-10-19 | 2011-10-04 | Ube Industries, Ltd. | Methods for producing perfluoroalkanedi(sulfonyl chloride) |
WO2009076345A1 (en) * | 2007-12-11 | 2009-06-18 | Im & T Research, Inc. | Methods and compositions for producing difluoromethylene-and trifluoromethyl-containing compounds |
TW201006787A (en) * | 2008-03-07 | 2010-02-16 | Im & T Res Inc | Fluorination processes with arylsulfur halotetrafluorides |
EP2323974A1 (en) * | 2008-08-18 | 2011-05-25 | Ube Industries, Ltd. | Methods for preparing fluoroalkyl arylsulfinyl compounds and fluorinated compounds thereto |
WO2010033930A1 (en) * | 2008-09-22 | 2010-03-25 | Im&T Research, Inc. | Processes for preparing poly(pentafluorosulfanyl)aromatic compounds |
US20100174096A1 (en) * | 2009-01-05 | 2010-07-08 | Im&T Research, Inc. | Methods for Production of Optically Active Fluoropyrrolidine Derivatives |
US8203003B2 (en) | 2009-01-09 | 2012-06-19 | Ube Industries, Ltd. | 4-fluoropyrrolidine-2-carbonyl fluoride compounds and their preparative methods |
US20120157716A1 (en) * | 2010-07-08 | 2012-06-21 | Ube Industries, Ltd. | Methods for Preparing Diaryl Disulfides |
WO2013118915A1 (en) * | 2012-02-09 | 2013-08-15 | Ube Industries, Ltd. | Processes for isolating fluorinated products |
JP6276852B2 (ja) | 2013-10-15 | 2018-02-07 | ジン,ボハン | 新規化合物、使用およびそれらの調製のための方法 |
CN105777594A (zh) * | 2014-12-26 | 2016-07-20 | 王建华 | 一种硫醇化合物的清洁生产方法 |
WO2018065182A1 (en) | 2016-10-04 | 2018-04-12 | Basf Se | Reduced quinoline compounds as antifuni agents |
JP7057489B2 (ja) | 2016-12-26 | 2022-04-20 | ダイキン工業株式会社 | ジフルオロメチレン化合物の製造方法 |
WO2018123890A1 (ja) | 2016-12-26 | 2018-07-05 | ダイキン工業株式会社 | ジフルオロメチレン化合物の製造方法 |
BR112019014061A2 (pt) | 2017-01-23 | 2020-02-04 | Basf Se | compostos de fórmula i, intermediários b, intermediários c, intermediários ii e intermediários d, composição, uso, método para combater fungos fitopatogênicos, semente e processo para a síntese dos compostos de fórmula i |
JP2020097528A (ja) * | 2017-04-03 | 2020-06-25 | 宇部興産株式会社 | トリフルオロスルファニル芳香族化合物を含む混合物の変性方法および分析方法 |
EP3606914A1 (en) | 2017-04-06 | 2020-02-12 | Basf Se | Pyridine compounds |
JP6974734B2 (ja) | 2018-04-25 | 2021-12-01 | ダイキン工業株式会社 | ジフルオロメチレン化合物の製造方法 |
CN110776446B (zh) * | 2019-11-26 | 2021-11-05 | 湖南新合新生物医药有限公司 | 二芳基二硫醚的制备方法 |
JPWO2021200640A1 (zh) * | 2020-03-31 | 2021-10-07 | ||
CN114773185B (zh) * | 2022-05-10 | 2023-01-03 | 南京理工大学 | 利用三氟甲基亚磺酸钠合成苯甲酰氟化合物的方法 |
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-
2006
- 2006-07-28 US US11/494,983 patent/US7265247B1/en active Active
- 2006-08-16 WO PCT/US2006/031963 patent/WO2008013550A1/en active Application Filing
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- 2007-07-25 KR KR1020097003734A patent/KR100949654B1/ko not_active IP Right Cessation
- 2007-07-25 EP EP07840515.6A patent/EP2046735B1/en active Active
- 2007-07-25 WO PCT/US2007/074359 patent/WO2008014345A2/en active Application Filing
- 2007-07-25 UA UAA200901550A patent/UA96301C2/ru unknown
- 2007-07-25 JP JP2009521991A patent/JP4531852B2/ja active Active
- 2007-07-25 CA CA2658364A patent/CA2658364C/en active Active
- 2007-07-27 TW TW096127607A patent/TWI325857B/zh active
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2009
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- 2010-09-20 US US12/886,286 patent/US8710270B2/en active Active
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- 2014-03-14 US US14/213,494 patent/US9365471B2/en active Active
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CA2658364A1 (en) | 2008-01-31 |
WO2008014345A2 (en) | 2008-01-31 |
JP2010195811A (ja) | 2010-09-09 |
US20080221364A1 (en) | 2008-09-11 |
WO2008014345A3 (en) | 2008-07-03 |
JP4531852B2 (ja) | 2010-08-25 |
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CA2658364C (en) | 2013-01-15 |
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US7501543B2 (en) | 2009-03-10 |
US7265247B1 (en) | 2007-09-04 |
TW200831451A (en) | 2008-08-01 |
UA96301C2 (ru) | 2011-10-25 |
TWI325857B (en) | 2010-06-11 |
RU2009106712A (ru) | 2010-09-10 |
WO2008013550A1 (en) | 2008-01-31 |
CN101522611A (zh) | 2009-09-02 |
RU2451011C2 (ru) | 2012-05-20 |
US9365471B2 (en) | 2016-06-14 |
US20110009672A1 (en) | 2011-01-13 |
JP2009544735A (ja) | 2009-12-17 |
US8710270B2 (en) | 2014-04-29 |
EP2046735B1 (en) | 2015-05-06 |
EP2046735A4 (en) | 2013-11-20 |
KR20090041413A (ko) | 2009-04-28 |
JP5234371B2 (ja) | 2013-07-10 |
US20080039660A1 (en) | 2008-02-14 |
US7919635B2 (en) | 2011-04-05 |
WO2008013550A8 (en) | 2008-04-10 |
US20140235898A1 (en) | 2014-08-21 |
KR100949654B1 (ko) | 2010-03-26 |
EP2046735A2 (en) | 2009-04-15 |
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