CN114014884A - Preparation method of aryl nitrogenous heterocyclic borate - Google Patents
Preparation method of aryl nitrogenous heterocyclic borate Download PDFInfo
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- CN114014884A CN114014884A CN202111438020.3A CN202111438020A CN114014884A CN 114014884 A CN114014884 A CN 114014884A CN 202111438020 A CN202111438020 A CN 202111438020A CN 114014884 A CN114014884 A CN 114014884A
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- borate
- aryl
- containing heterocyclic
- nitrogen
- heterocyclic borate
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- 125000003118 aryl group Chemical group 0.000 title claims abstract description 21
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 20
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 19
- -1 aryl nitrogenous heterocyclic borate ester Chemical class 0.000 claims abstract description 14
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims abstract description 13
- ZYGAMJLTPLERBC-UHFFFAOYSA-N (3-hydroxy-2,3-dimethylbutan-2-yl)oxyboronic acid propan-2-ol Chemical compound B(O)(O)OC(C)(C)C(C)(C)O.C(C)(C)O ZYGAMJLTPLERBC-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 239000011261 inert gas Substances 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 6
- 235000019270 ammonium chloride Nutrition 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 238000010791 quenching Methods 0.000 claims description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 6
- 235000011152 sodium sulphate Nutrition 0.000 claims description 6
- 239000008247 solid mixture Substances 0.000 claims description 6
- 239000012265 solid product Substances 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 230000000171 quenching effect Effects 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 11
- 238000003786 synthesis reaction Methods 0.000 abstract description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 4
- 150000001642 boronic acid derivatives Chemical class 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 150000001502 aryl halides Chemical class 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000001465 metallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- 150000001500 aryl chlorides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
Abstract
The invention discloses a preparation method of aryl nitrogenous heterocyclic borate, which comprises the following specific steps: the method comprises the following steps of taking 2- (3-bromophenyl) -3,5, 6-triphenylpropylamine and isopropanol pinacol borate as reaction raw materials, taking n-butyl lithium as a catalyst, and fully reacting at room temperature under the protection of inert gas to obtain the target product, namely the aryl nitrogen-containing heterocyclic borate. On the basis of the existing synthesis process research, the invention forms a new synthesis process of the aryl nitrogenous heterocyclic borate ester by optimally designing raw materials, catalysts and key process parameters, and finally achieves the purposes of simple operation, suitability for amplified production, high product yield and good product purity.
Description
Technical Field
The invention belongs to the technical field of synthesis of aryl borate compounds, and particularly relates to a preparation method of aryl nitrogenous heterocyclic borate.
Background
Organoboron chemistry has been developed over a hundred years since the first synthesis of organoboron compounds by Ebelman and obuque in 1846. In particular, the rapid development has been made in recent decades, and a large number of organoboronate compounds are synthesized one after another and widely used in production practice. The organic borate compounds can be used as a plasticizer, a fluxing agent in the welding process, a textile flame retardant and the like, and can also be used as a multifunctional additive, a neutron absorber and a main raw material for synthesizing organic boron compounds; and borate compounds having new functions and uses are also being continuously developed because of their high molecular designability. Therefore, the synthesis and performance research of the compound has been paid attention.
The synthesis method of the borate compounds is various. The traditional method is a Grignard reagent and lithium reagent method, namely aryl bromide or iodide is adopted for metallization, corresponding Grignard reagent or organic lithium reagent is prepared, and then boron reagent is used for boronization. The method has the advantages of harsh metallization reaction conditions, poor functional group compatibility and low yield, is not suitable for aryl chloride, and is greatly limited in application. With the advent of metal catalysis, methods for catalytically synthesizing arylboronic acid ester compounds by using palladium, copper, nickel, rhodium, iridium, ruthenium and the like as catalysts have been developed. Among them, the palladium catalysis method has made a great progress in recent ten years, and becomes a method with a good effect of synthesizing arylboronic acid ester compounds, and has the characteristics of good functional group tolerance, high yield and the like. Although the palladium catalysis method is better applied to the synthesis of aryl borate by adopting aryl halides (mainly bromide and iodide) or aryl triflate, the reaction is carried out under the conditions of no water and oxygen, high temperature and tube sealing, and the defects of harsh reaction conditions, large catalyst dosage, unsuitability for large-scale preparation and the like exist. In addition, the method for efficiently preparing the corresponding aryl borate compound by using the aryl halide which is low in price, easy to obtain and diverse in structure as a raw material has fewer reports.
Disclosure of Invention
The invention solves the technical problem of providing a preparation method of aryl nitrogenous heterocyclic borate, which has wide application range, small catalyst consumption and high synthesis efficiency, and the preparation method forms a new synthesis process of the aryl nitrogenous heterocyclic borate by optimally designing raw materials, catalysts and key process parameters on the basis of the research of the existing synthesis process, finally achieves the purposes of simple operation, suitability for amplified production, higher product yield and better product purity, effectively overcomes the defects of the existing synthesis process, and has important practical significance.
The invention adopts the following technical scheme for solving the technical problems, and the preparation method of the aryl nitrogenous heterocyclic borate is characterized by comprising the following specific steps: taking 2- (3-bromophenyl) -3,5, 6-triphenylpropylamine and isopropanol pinacol borate as reaction raw materials, taking n-butyl lithium as a catalyst, and fully reacting at room temperature under the protection of inert gas to prepare the target product, namely the aryl nitrogen-containing heterocyclic borate, wherein the synthetic route in the preparation process is as follows:
the feeding molar ratio of the 2- (3-bromophenyl) -3,5, 6-triphenylpropylamine to the isopropanol pinacol borate is 1-1.5: 3.
Further limited, the preparation method of the aryl nitrogen-containing heterocyclic borate is characterized by comprising the following specific steps: under the protection of inert gas, dissolving 2- (3-bromophenyl) -3,5, 6-triphenylpropylamine in an ether organic solvent, reducing the temperature of a reactor to-100 to-30 ℃ by using liquid nitrogen, dropwise adding n-butyllithium n-hexane solution when the temperature is constant, and incubating; and dropwise adding isopropanol pinacol borate at a low temperature, naturally heating to room temperature for full reaction, adding an ammonium chloride aqueous solution after the reaction is finished, quenching the reaction, extracting by using a non-water-soluble organic solvent, washing the liquid, drying by using sodium sulfate, concentrating under reduced pressure to obtain a yellow solid mixture, dispersing by using an n-hexane solution, cooling, filtering and drying to obtain a white solid product, namely the aromatic group nitrogen-containing heterocyclic borate with the purity of over 95%.
Further, the temperature of the low temperature condition is-100 to-50 ℃, preferably-80 to-70 ℃.
Further limiting, the sufficient reaction time is 6-10 h, preferably 6-8 h, and more preferably 7-8 h.
Further defined, the ether organic solvent is one or more of tetrahydrofuran, methyl tetrahydrofuran, diethyl ether or methyl tert-butyl ether.
Further defined, the water-insoluble organic solvent is one or more of ethyl acetate, methyl acetate or tetrahydrofuran.
The mass ratio of the 2- (3-bromophenyl) -3,5, 6-tripropylamine to the n-butyllithium n-hexane solution is further limited to 1: 1.15-3.
Compared with the prior art, the invention has the following advantages and beneficial effects: the invention provides the preparation method of the aromatic group nitrogen-containing heterocyclic borate, which has the advantages of wide application range, small catalyst consumption and high efficiency for the first time, overcomes the defects of the existing synthesis process, and has important practical significance. And secondly, the reaction process provided by the invention selects raw materials, temperature, conditions and the like, has the characteristics of mild reaction conditions, simplicity and convenience in operation, no by-product and high yield, and has remarkable social benefit.
Detailed Description
The present invention is described in further detail below with reference to examples, but it should not be construed that the scope of the above subject matter of the present invention is limited to the following examples, and that all the technologies realized based on the above subject matter of the present invention belong to the scope of the present invention.
Example 1
Under the protection of inert gas argon, adding 50g of 2- (3-bromophenyl) -3,5, 6-triphenylpropylamine into 200mL of tetrahydrofuran solvent, reducing the temperature of the reactor to-78 ℃ by using liquid nitrogen, dropwise adding 52mL of 2.5M n-butyllithium n-hexane solution when the temperature is constant, and incubating for 1 h; and slowly dripping 40g of isopropanol pinacol borate at a low temperature, naturally heating to room temperature to fully react for 8 hours, adding an ammonium chloride aqueous solution with the same volume as the reaction solution after the reaction is finished to quench the reaction, extracting with ethyl acetate, washing the separated liquid, drying with sodium sulfate, concentrating under reduced pressure to obtain a yellow solid mixture, dispersing with an n-hexane solution, cooling, filtering and drying to obtain a white solid product, namely the aromatic group nitrogen-containing heterocyclic borate.
H NMR(DMSOd6,400MHz)δ:8.229～7.216(m,19H,-Ar-H),1.327(m,12H，-C-C-H)。
Example 2
Under the protection of inert gas argon, adding 50g of 2- (3-bromophenyl) -3,5, 6-triphenylpropylamine into 200mL of tetrahydrofuran solvent, reducing the temperature of the reactor to-85 ℃ by using liquid nitrogen, dropwise adding 52mL of 2.5M n-butyllithium n-hexane solution when the temperature is constant, and incubating for 1 h; and slowly dripping 40g of isopropanol pinacol borate at a low temperature, naturally heating to room temperature to fully react for 8 hours, adding an ammonium chloride aqueous solution with the same volume as the reaction solution after the reaction is finished to quench the reaction, extracting with ethyl acetate, washing the separated liquid, drying with sodium sulfate, concentrating under reduced pressure to obtain a yellow solid mixture, dispersing with an n-hexane solution, cooling, filtering and drying to obtain a white solid product, namely the aromatic group nitrogen-containing heterocyclic borate.
H NMR(DMSOd6,400MHz)δ:8.229～7.216(m,19H,-Ar-H),1.327(m,12H，-C-C-H)。
Example 3
Under the protection of inert gas argon, adding 50g of 2- (3-bromophenyl) -3,5, 6-tripropylamine into 250mL of methyl tetrahydrofuran solvent, reducing the temperature of the reactor to-85 ℃ by using liquid nitrogen under the low-temperature condition, dropwise adding 52mL of 2.5M n-butyllithium n-hexane solution when the temperature is constant, and incubating for 1 h; and slowly dripping 40g of isopropanol pinacol borate at a low temperature, naturally heating to room temperature to fully react for 8 hours, adding an ammonium chloride aqueous solution with the same volume as the reaction solution after the reaction is finished to quench the reaction, extracting with ethyl acetate, washing the separated liquid, drying with sodium sulfate, concentrating under reduced pressure to obtain a yellow solid mixture, dispersing with an n-hexane solution, cooling, filtering and drying to obtain a white solid product, namely the aromatic group nitrogen-containing heterocyclic borate.
H NMR(DMSOd6,400MHz)δ:8.229～7.216(m,19H,-Ar-H),1.327(m,12H，-C-C-H)。
Example 4
Under the protection of inert gas argon, adding 50g of 2- (3-bromophenyl) -3,5, 6-tripropylamine into 250mL of methyl tetrahydrofuran solvent, reducing the temperature of the reactor to-85 ℃ by using liquid nitrogen under the low-temperature condition, dropwise adding 52mL of 2.5M n-butyllithium n-hexane solution when the temperature is constant, and incubating for 1 h; and slowly dripping 40g of isopropanol pinacol borate at a low temperature, naturally heating to room temperature to perform full reaction for 10 hours, adding an ammonium chloride aqueous solution with the same volume as the reaction solution after the reaction is finished to perform quenching reaction, extracting with ethyl acetate, washing with water, separating liquid, drying with sodium sulfate, performing reduced pressure concentration to obtain a yellow solid mixture, dispersing with an n-hexane solution, cooling, filtering and drying to obtain a white solid product, namely the aromatic group nitrogen-containing heterocyclic borate.
H NMR(DMSOd6,400MHz)δ:8.229～7.216(m,19H,-Ar-H),1.327(m,12H，-C-C-H)。
The target product prepared in the embodiment 1-4 is aryl nitrogen heterocyclic borate, and the chromatographic purity of the product is more than 95%.
While there have been shown and described what are at present considered the fundamental principles of the invention, its essential features and advantages, the invention further resides in various changes and modifications which fall within the scope of the invention as claimed.
Claims (8)
1. A preparation method of aryl nitrogen heterocyclic borate is characterized by comprising the following specific steps: taking 2- (3-bromophenyl) -3,5, 6-triphenylpropylamine and isopropanol pinacol borate as reaction raw materials, taking n-butyl lithium as a catalyst, and fully reacting at room temperature under the protection of inert gas to prepare the target product, namely the aryl nitrogen-containing heterocyclic borate, wherein the synthetic route in the preparation process is as follows:
2. the method for producing an aromatic group nitrogen-containing heterocyclic borate ester according to claim 1, characterized in that: the feeding molar ratio of the 2- (3-bromophenyl) -3,5, 6-triphenylpropylamine to the isopropanol pinacol borate is 1-1.5: 3.
3. The method for preparing the aryl nitrogen-containing heterocyclic borate ester according to claim 1, which comprises the following steps: under the protection of inert gas, dissolving 2- (3-bromophenyl) -3,5, 6-triphenylpropylamine in an ether organic solvent, reducing the temperature of a reactor to-100 to-30 ℃ by using liquid nitrogen, dropwise adding n-butyllithium n-hexane solution when the temperature is constant, and incubating; and dropwise adding isopropanol pinacol borate at a low temperature, naturally heating to room temperature for full reaction, adding an ammonium chloride aqueous solution after the reaction is finished, quenching the reaction, extracting by using a non-water-soluble organic solvent, washing the liquid, drying by using sodium sulfate, concentrating under reduced pressure to obtain a yellow solid mixture, dispersing by using an n-hexane solution, cooling, filtering and drying to obtain a white solid product, namely the aromatic group nitrogen-containing heterocyclic borate with the purity of over 95%.
4. The method for producing an aryl nitrogen-containing heterocyclic borate ester according to claim 3, characterized in that: the temperature of the low-temperature condition is-100 to-50 ℃.
5. The method for producing an aryl nitrogen-containing heterocyclic borate ester according to claim 3, characterized in that: the sufficient reaction time is 6-10 h.
6. The method for producing an aryl nitrogen-containing heterocyclic borate ester according to claim 3, characterized in that: the ether organic solvent is one or more of tetrahydrofuran, methyl tetrahydrofuran, diethyl ether or methyl tert-butyl ether.
7. The method for producing an aryl nitrogen-containing heterocyclic borate ester according to claim 3, characterized in that: the water-insoluble organic solvent is one or more of ethyl acetate, methyl acetate or tetrahydrofuran.
8. The method for producing an aryl nitrogen-containing heterocyclic borate ester according to claim 3, characterized in that: the feeding mass ratio of the 2- (3-bromophenyl) -3,5, 6-tripropylamine to the n-butyllithium n-hexane solution is 1: 1.15-3.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111793080A (en) * | 2020-08-11 | 2020-10-20 | 山东卓俊实业有限公司 | Preparation method of aryl boric acid ester |
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| CN112368858A (en) * | 2018-06-14 | 2021-02-12 | 诺瓦尔德股份有限公司 | Organic material for electronic optoelectronic devices and electronic devices comprising said organic material |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112368858A (en) * | 2018-06-14 | 2021-02-12 | 诺瓦尔德股份有限公司 | Organic material for electronic optoelectronic devices and electronic devices comprising said organic material |
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| Title |
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| MING CHEN等: "Tailoring the Molecular Properties with Isomerism Effect of AIEgens", ADV. FUNCT. MATER., vol. 29, pages 1 - 12 * |
Cited By (2)
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|---|---|---|---|---|
| CN111793080A (en) * | 2020-08-11 | 2020-10-20 | 山东卓俊实业有限公司 | Preparation method of aryl boric acid ester |
| CN111793080B (en) * | 2020-08-11 | 2022-07-01 | 山东益健药业有限公司 | Preparation method of aryl boric acid ester |
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