CN104610068A - Preparation method of 2,4,6-trifluoro-benzylamine compound - Google Patents
Preparation method of 2,4,6-trifluoro-benzylamine compound Download PDFInfo
- Publication number
- CN104610068A CN104610068A CN201410853129.7A CN201410853129A CN104610068A CN 104610068 A CN104610068 A CN 104610068A CN 201410853129 A CN201410853129 A CN 201410853129A CN 104610068 A CN104610068 A CN 104610068A
- Authority
- CN
- China
- Prior art keywords
- preferred
- trifluoro
- tri
- thf
- tetrahydrofuran
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of a 2,4,6-trifluoro-benzylamine compound. The preparation method comprises the following steps: taking 1,3,5-trifluoro-benzene as a raw material, and preparing 2,4,6-trifluoro-benzylamine through lithiation, formylation, reduction, halogenation and replacement reaction. The reaction condition is mild, the operability is high, the atom economy is high, the technology is simple and easy to realize industrialization, and the product is high in purity and stable in quality, so that the compound accords with the using requirement of being as an intermediate.
Description
Technical field
The present invention relates to pesticide imidacloprid, acetamiprid and medical mafenide intermediate field, be specifically related to the preparation method field of 2,4,6-tri-flunamine.
Current end sees that this product is reported accordingly, but has the report of like product 2,6-difluorobenzylamine, and it obtains 2,6-difluorobenzylamine with 2,6-difluorobenzonilyile Hydrogenation under nickel catalysis.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of 2,4,6-tri-flunamine, is realized by following reaction:
A kind of preparation method of 2,4,6-tri-flunamine, comprises the following steps:
Concrete steps are:
(1) 1,3,5-trifluoro-benzene at-50 ~-110 DEG C, preferably lithiumation, use in organic solvent under the cold condition of-55 ~-90 DEG C
DMF (DMF) replaces the lithium on benzene, then obtains 2,4,6-trifluro benzaldehyde through hydrolysis;
(2) 2,4,6-trifluro benzaldehydes obtain 2,4,6-tri-fluoro benzyl alcohol with potassium borohydride reduction in organic solvent;
(3) 2,4,6-tri-fluoro benzyl alcohols react generation 2,4,6-trifluoro benzyl chlorine in organic solvent with sulfur oxychloride;
(4) 2,4,6-trifluoro benzyl chlorine are hydrolyzed with urotropine salify again and obtain final product 2,4,6-tri-flunamine in ethanol system.
As one embodiment of the invention, described in step (1), organic solvent is selected from tetrahydrofuran (THF), methyl tertiary butyl ether and toluene, preferred tetrahydrofuran (THF).
As one embodiment of the invention, in step (1), the mass ratio of 1,3,5-trifluoro-benzene and solvent for use is 1:(1 ~ 7), preferred 1:(2 ~ 5).
As one embodiment of the invention, in step (1), the mol ratio of 1,3,5-trifluoro-benzene and butyllithium is 1:(0.8 ~ 1.5), preferred 1:(1 ~ 1.2).
As one embodiment of the invention, in step (1), the mol ratio of 1,3,5-trifluoro-benzene and DMF is 1:(0.8 ~ 2), preferred 1:(1 ~ 1.5).
As one embodiment of the invention, described in step (2), organic solvent is selected from ethanol, tetrahydrofuran (THF), toluene and methyl tertiary butyl ether, preferred alcohol.
As one embodiment of the invention, in step (2), the mass ratio of 2,4,6-trifluro benzaldehydes and organic solvent used is 1:(1 ~ 5), preferred 1:(1 ~ 3).
As one embodiment of the invention, in step (2), temperature of reaction is 20 ~ 60 DEG C, preferably 30 ~ 40 DEG C;
As one embodiment of the invention, step (2) is carried out in the presence of a reducing agent, and described reductive agent is POTASSIUM BOROHYDRIDE or sodium borohydride, preferred POTASSIUM BOROHYDRIDE.
As one embodiment of the invention, mol ratio 1:(0.2 ~ 0.8 of 2,4,6-trifluro benzaldehydes and reductive agent in step (2)), preferred 1:(0.3 ~ 0.5).
As one embodiment of the invention, described in step (3), organic solvent is selected from tetrahydrofuran (THF), methyl alcohol, ethanol, toluene and methylene dichloride, preferred tetrahydrofuran (THF).
As one embodiment of the invention, in step (3), the mass ratio of 2,4,6-tri-fluoro benzyl alcohols and organic solvent is 1:(0.5 ~ 5), preferred 1:(1.5 ~ 3); Temperature of reaction is 15 ~ 60 DEG C, preferably 30 ~ 50 DEG C.
As one embodiment of the invention, 2,4,6-tri-fluoro benzyl alcohols and chlorizating agent halogenating reaction in step (3), chlorizating agent is selected from sulfur oxychloride, N-chlorosuccinimide and chlorine, preferred sulfur oxychloride.
As one embodiment of the invention, in step (3), the mol ratio of 2,4,6-tri-fluoro benzyl alcohols and chlorizating agent is 1:(0.8 ~ 2.5), be preferably 1:(1 ~ 1.6).
As one embodiment of the invention, step (4) is carried out in the presence of solvent, described solvent selected from methanol, ethanol, tetrahydrofuran (THF), normal hexane and toluene, preferred tetrahydrofuran (THF).
As one embodiment of the invention, in step (4), the mass ratio of 2,4,6-trifluoro benzyl chlorine and solvent is 1:(1 ~ 8), preferred 1:(3 ~ 6).
As one embodiment of the invention, in step (4), the salt-forming reaction temperature of 2,4,6-trifluoro benzyl chlorine and urotropine is 20 ~ 80 DEG C, is preferably 50 ~ 70 DEG C.
As one embodiment of the invention, the temperature be hydrolyzed after 2,4,6-trifluoro benzyl chlorine and urotropine salify in step (4) is 20 ~ 60 DEG C, is preferably 30 ~ 40 DEG C.
Embodiment
Following type reaction is used for illustrating the present invention.All belong within the technical scheme that the present invention protects inventing the simple replacement done or improvement etc. those skilled in that art.
The preparation of embodiment 1:2,4,6-trifluro benzaldehyde
2000ml four-hole bottle drops into tetrahydrofuran (THF) 500g, and 1,3,5-trifluoro-benzene 132g, is cooled to-60 DEG C, drips 2.5N 500ml butyllithium at-60 ~-90 DEG C, drip about 1.5h, finish insulation 2h, system drips 80g N, dinethylformamide and 100g tetrahydrofuran solution, control temperature, below-60 DEG C, finishes insulation reaction 3h, and insulation is finished, be warming up to-30 DEG C, stand-by.Drop into 650g water, 226g30% hydrochloric acid, 190g sodium-chlor in another 3000ml four-hole bottle, stir, drip above-mentioned low-temp reaction liquid at 20 DEG C, finish, insulation 0.5h, layering, water layer 200g methyl tertiary butyl ether extracts, merge organic layer, boil off solvent and obtain 2,4,6-trifluro benzaldehyde 145g, GC:97%, yield 90%.
Gained final product carries out mass spectroscopy and ultimate analysis, and acquired results is as follows:
Mass spectrum: m/z:160.01 (100.0%), 161.02 (7.6%).
Ultimate analysis: C, 52.52; H, 1.89; F, 35.60; O, 9.99.
Can determine to obtain 2,4,6-trifluro benzaldehyde.
The preparation of embodiment 2:2,4,6-trifluro benzaldehyde
By embodiment 1, replace 500ml n-Butyl Lithium with 400ml n-Butyl Lithium, be obtained by reacting 2,4,6-trifluro benzaldehyde 116g, GC97.2%, yield 72.5%.
The preparation of embodiment 3:2,4,6-trifluro benzaldehyde
By embodiment 1, replace 500ml n-Butyl Lithium with 550ml n-Butyl Lithium, be obtained by reacting 2,4,6-trifluro benzaldehyde 155g, GC:88.2%, yield 85%.
The preparation of embodiment 4:2,4,6-trifluro benzaldehyde
By embodiment 1, with 70gN, dinethylformamide consumption replaces 80gN, and dinethylformamide consumption, is obtained by reacting 2,4,6-trifluro benzaldehyde 132g GC:97.9%, yield 82.5%.
The preparation of embodiment 5:2,4,6-trifluro benzaldehyde
By embodiment 1, replace 80gDMF with 100gDMF, be obtained by reacting 2,4,6-trifluro benzaldehyde 148gGC:95.1%, yield 87.8%.
Embodiment 6:2,4,6-tri-preparation of fluoro benzyl alcohol
2000ml four-hole bottle drops into 17.2g POTASSIUM BOROHYDRIDE and 100g ethanol, is warming up to 30 DEG C, drips 138g2,4,6-trifluro benzaldehyde and 200g ethanolic soln, control temperature is below 35 DEG C, finish insulation reaction, middle control to without raw material, stopped reaction, solvent evaporated, the 600g that adds water in reaction flask is stirred to entirely molten, layering, water layer 150g methyl tertiary butyl ether extracts, merge organic layer desolventizing, distill to obtain 117g GC:96.2%, yield 86%.
Gained final product carries out mass spectroscopy and ultimate analysis, and acquired results is as follows:
Mass spectrum: m/z:162.03 (100.0%), 163.03 (7.6%).
Ultimate analysis: C, 51.86; H, 3.11; F, 35.16; O, 9.87.
Can determine to obtain 2,4,6-tri-fluoro benzyl alcohol.
Embodiment 7:2,4,6-tri-preparation of fluoro benzyl alcohol
By embodiment 6, replace 100g ethanol with 100g methyl alcohol, be obtained by reacting 2,4,6-tri-fluoro benzyl alcohol 112g GC:95.4%, yield 82.3%.
Embodiment 8:2,4,6-tri-preparation of fluoro benzyl alcohol
By embodiment 6, replace 100g ethanol with 100g tetrahydrofuran (THF), be obtained by reacting 2,4,6-tri-fluoro benzyl alcohol 118.8g, GC:96.5%, yield 86.1%
Embodiment 9:2,4,6-tri-preparation of fluoro benzyl alcohol
By embodiment 6, replace 17.2g POTASSIUM BOROHYDRIDE with 15g POTASSIUM BOROHYDRIDE, be obtained by reacting 2,4,6-tri-fluoro benzyl alcohol 118g, GC:92.2%, yield 78.8%.
Embodiment 10:2,4,6-tri-preparation of fluoro benzyl alcohol
By embodiment 6, replace 17.2g POTASSIUM BOROHYDRIDE with 20g POTASSIUM BOROHYDRIDE, be obtained by reacting 2,4,6-tri-fluoro benzyl alcohol 115.6g, GC:97%, yield 84%.
The preparation of embodiment 11:2,4,6-trifluoro benzyl chlorine
2000ml four-hole bottle drops into 171.6g 2,4,6-tri-fluoro benzyl alcohol, 316g tetrahydrofuran (THF) and 106g pyridine, be cooled to 20 DEG C, drip 160g sulfur oxychloride, control temperature, not higher than 30 DEG C, finishes about 1.5h, after dropping terminates, be warming up to 50 DEG C of reactions, middle control is extremely without raw material and intermediate, be cooled to 20 DEG C, add 500g water, stir 30min, stratification, water layer 150g dichloromethane extraction, merges organic layer, recycling design, obtains material 176g GC:94.1%, yield 91.4%.
Gained final product carries out mass spectroscopy and ultimate analysis, and acquired results is as follows:
Mass spectrum: m/z:145.03 (100.0%), 146.03 (7.6%).
Ultimate analysis: C, 57.94; H, 2.78; F, 39.28.
Can determine to obtain 2,4,6-trifluoro benzyl chlorine.
The preparation of embodiment 12:2,4,6-trifluoro benzyl chlorine
By embodiment 11, replace 316g tetrahydrofuran (THF) with 300g methyl alcohol, be obtained by reacting 2,4,6-trifluoro benzyl chlorine 164g, GC:95%, yield 86%.
The preparation of embodiment 13:2,4,6-trifluoro benzyl chlorine
By embodiment 11, replace 316g tetrahydrofuran (THF) with 300g ethanol, be obtained by reacting 2,4,6-trifluoro benzyl chlorine 166g, GC:94.6%, yield 86.6%.
The preparation of embodiment 14:2,4,6-trifluoro benzyl chlorine
By embodiment 11, replace 106g pyridine with 80g pyridine, be obtained by reacting 2,4,6-trifluoro benzyl chlorine 158g, GC:86.4%, yield 71%.
Embodiment 15:2,4,6-tri-preparation of flunamine
2000ml four-hole bottle drops into 700g ethanol, 141g urotropine, be warming up to 65 DEG C, drip 134g 2 under reflux, 4, 6-trifluoro benzyl chlorine, rate of addition is equal with backflow, time for adding 1h, finish in insulation reaction and control extremely without raw material, soaking time 5h, be cooled to 20 DEG C, drip 450g36% hydrochloric acid, finish to be warming up in 40 DEG C of insulation reaction and control without intermediate, insulation 4h, be cooled to 15 DEG C, cross the salt in the system of filtering, filtrate recycling ethanol, steam extremely without flow, 1500g water is added in the molten device of reaction, be stirred to entirely molten, add 10g activated carbon decolorizing, obtain clear filtrate and add 180g 30% liquid caustic soda tune PH12, stratification, obtain organic layer, water layer 200g dichloromethane extraction twice, merge organic layer, recycling design, distill to obtain product 98.2g, GC:98.96%, yield 82.5%.
Gained final product carries out mass spectroscopy and ultimate analysis, and acquired results is as follows:
Mass spectrum: m/z:161.05 (100.0%), 162.05 (7.6%).
Ultimate analysis: C, 52.18; H, 3.75; F, 35.57; N, 8.69.
Can determine to obtain 2,4,6-tri-flunamine.
The preparation of embodiment 16:2,4,6-trifluoro benzyl chlorine
By embodiment 15, replace 700g ethanol with 700g tetrahydrofuran (THF), be obtained by reacting 2,4,6-tri-flunamine 99.6g, GC99.07%, yield 83.7%.
Embodiment 17:2,4,6-tri-preparation of flunamine
By embodiment 15, replace 141g urotropine with 110g urotropine, be obtained by reacting 2,4,6-tri-flunamine 92.8g, GC98.6%, yield 78%.
Claims (10)
1. the preparation method of tri-flunamines, is characterized in that comprising the following steps:
(1) 1,3,5-trifluoro-benzene at-50 ~-110 DEG C, preferably under the cold condition of-55 ~-90 DEG C in organic solvent lithiumation, replace the lithium on benzene with DMF, then obtain 2,4,6-trifluro benzaldehyde through hydrolysis;
(2) 2,4,6-trifluro benzaldehydes obtain 2,4,6-tri-fluoro benzyl alcohol with potassium borohydride reduction in organic solvent;
(3) 2,4,6-tri-fluoro benzyl alcohols react generation 2,4,6-trifluoro benzyl chlorine in organic solvent with sulfur oxychloride;
(4) 2,4,6-trifluoro benzyl chlorine are hydrolyzed with urotropine salify again and obtain final product 2,4,6-tri-flunamine in ethanol system.
2. method according to claim 1, is characterized in that described in step (1), organic solvent is selected from tetrahydrofuran (THF), methyl tertiary butyl ether and toluene, preferred tetrahydrofuran (THF); The mass ratio of 1,3,5-trifluoro-benzene and solvent for use is 1:(1 ~ 7), preferred 1:(2 ~ 5); In step (1), the mol ratio of 1,3,5-trifluoro-benzene and butyllithium is 1:(0.8 ~ 1.5), preferred 1:(1 ~ 1.2); The mol ratio of 1,3,5-trifluoro-benzene and DMF is 1:(0.8 ~ 2), preferred 1:(1 ~ 1.5).
3. method according to claim 1, it is characterized in that step (2) is carried out in the presence of a reducing agent, described reductive agent is POTASSIUM BOROHYDRIDE or sodium borohydride, preferred POTASSIUM BOROHYDRIDE; Mol ratio 1:(0.2 ~ 0.8 of 2,4,6-trifluro benzaldehyde and reductive agent), preferred 1:(0.3 ~ 0.5).
4. method according to claim 1, is characterized in that described in step (2), organic solvent is selected from ethanol, tetrahydrofuran (THF), toluene and methyl tertiary butyl ether, preferred alcohol; The mass ratio of 2,4,6-trifluro benzaldehyde and organic solvent used is 1:(1 ~ 5), preferred 1:(1 ~ 3); Temperature of reaction is 20 ~ 60 DEG C, preferably 30 ~ 40 DEG C.
5. method according to claim 1, it is characterized in that described in step (3), organic solvent is selected from tetrahydrofuran (THF), methyl alcohol, ethanol, toluene and methylene dichloride, preferred tetrahydrofuran (THF), 2,4, the mass ratio of 6-tri-fluoro benzyl alcohol and organic solvent is 1:(0.5 ~ 5), preferred 1:(1.5 ~ 3); Temperature of reaction is 15 ~ 60 DEG C, preferably 30 ~ 50 DEG C.
6. method according to claim 1, to it is characterized in that in step (3) 2,4,6-tri-fluoro benzyl alcohol and chlorizating agent halogenating reaction, chlorizating agent is selected from sulfur oxychloride, N-chlorosuccinimide and chlorine, preferred sulfur oxychloride, 2, the mol ratio of 4,6-tri-fluoro benzyl alcohol and chlorizating agent is 1:(0.8 ~ 2.5), be preferably 1:(1 ~ 1.6).
7. method according to claim 1, is characterized in that step (4) is carried out in the presence of solvent, described solvent selected from methanol, ethanol, tetrahydrofuran (THF), normal hexane and toluene, preferred tetrahydrofuran (THF).
8. method according to claim 1, is characterized in that the mass ratio of 2,4,6-trifluoro benzyl chlorine and solvent in step (4) is 1:(1 ~ 8), preferred 1:(3 ~ 6).
9. method according to claim 1, is characterized in that the salt-forming reaction temperature of 2,4,6-trifluoro benzyl chlorine and urotropine in step (4) is 20 ~ 80 DEG C, is preferably 50 ~ 70 DEG C.
10. method according to claim 1, is characterized in that the temperature be hydrolyzed after 2,4,6-trifluoro benzyl chlorine and urotropine salify in step (4) is 20 ~ 60 DEG C, is preferably 30 ~ 40 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410853129.7A CN104610068B (en) | 2014-12-31 | 2014-12-31 | A kind of preparation method of 2,4,6-trifluoro benzylamine compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410853129.7A CN104610068B (en) | 2014-12-31 | 2014-12-31 | A kind of preparation method of 2,4,6-trifluoro benzylamine compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104610068A true CN104610068A (en) | 2015-05-13 |
| CN104610068B CN104610068B (en) | 2016-03-09 |
Family
ID=53144759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410853129.7A Active CN104610068B (en) | 2014-12-31 | 2014-12-31 | A kind of preparation method of 2,4,6-trifluoro benzylamine compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104610068B (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105017026A (en) * | 2015-07-02 | 2015-11-04 | 南京杰运医药科技有限公司 | Synthetic method of 2,4-difluorobenzene methylamine |
| CN107043322A (en) * | 2016-08-31 | 2017-08-15 | 绍兴上虞华伦化工有限公司 | A kind of preparation method of 2,4,6 trifluro benzaldehyde |
| CN107778183A (en) * | 2016-08-24 | 2018-03-09 | 杭州澳赛诺生物科技有限公司 | The preparation method of 2,4,6 3 fluorin benzyl amines |
| CN108530301A (en) * | 2018-06-04 | 2018-09-14 | 上海吉奉生物科技有限公司 | A kind of synthetic method of tri- fluorin benzyl amines of 2,4,6- |
| CN108892616A (en) * | 2018-08-31 | 2018-11-27 | 凯莱英生命科学技术(天津)有限公司 | Prepare continuous device and its application of benzaldehydes intermediate |
| CN110386864A (en) * | 2019-08-15 | 2019-10-29 | 天津凯莱英制药有限公司 | The method for continuously synthesizing of 2,4,6- trifluro benzaldehydes |
| CN110963922A (en) * | 2018-09-30 | 2020-04-07 | 成都博腾药业有限公司 | Preparation method of 2, 4, 6-trifluoro-benzene methylamine |
| CN111499540A (en) * | 2020-04-22 | 2020-08-07 | 中南民族大学 | Method for preparing 2,4,6-trichlorobenzonitrile by ammoxidation method, special catalyst and preparation method |
| CN114773147A (en) * | 2022-05-10 | 2022-07-22 | 浙江永太科技股份有限公司 | Preparation method of 2,4, 5-trifluorobenzyl bromide |
| CN115745766A (en) * | 2022-10-27 | 2023-03-07 | 兰州康鹏威耳化工有限公司 | Preparation method of trifluorobenzaldehyde and trifluorobenzyl bromide |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008037607A1 (en) * | 2006-09-25 | 2008-04-03 | Basf Se | Heterocyclic compounds containing carbonyl groups, and the use thereof for controlling phytopathogenic fungi |
-
2014
- 2014-12-31 CN CN201410853129.7A patent/CN104610068B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008037607A1 (en) * | 2006-09-25 | 2008-04-03 | Basf Se | Heterocyclic compounds containing carbonyl groups, and the use thereof for controlling phytopathogenic fungi |
Non-Patent Citations (3)
| Title |
|---|
| 中国技术成果大全编辑部: "《中国技术成果大全》", 31 January 1991, article "中国技术成果大全", pages: 233 * |
| 乐长高 主编: "《有机化学》", 31 August 2012, article "有机化学", pages: 178 * |
| 黄培强 主编: "《有机人名反应试剂与规则》", 31 January 2008, article "有机人名反应试剂与规则", pages: 153 * |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105017026A (en) * | 2015-07-02 | 2015-11-04 | 南京杰运医药科技有限公司 | Synthetic method of 2,4-difluorobenzene methylamine |
| CN107778183A (en) * | 2016-08-24 | 2018-03-09 | 杭州澳赛诺生物科技有限公司 | The preparation method of 2,4,6 3 fluorin benzyl amines |
| CN107778183B (en) * | 2016-08-24 | 2020-05-22 | 杭州澳赛诺生物科技有限公司 | Preparation method of 2,4, 6-trifluorobenzylamine |
| CN107043322A (en) * | 2016-08-31 | 2017-08-15 | 绍兴上虞华伦化工有限公司 | A kind of preparation method of 2,4,6 trifluro benzaldehyde |
| CN108530301A (en) * | 2018-06-04 | 2018-09-14 | 上海吉奉生物科技有限公司 | A kind of synthetic method of tri- fluorin benzyl amines of 2,4,6- |
| CN108530301B (en) * | 2018-06-04 | 2020-11-20 | 上海吉奉生物科技有限公司 | Synthetic method of 2,4, 6-trifluorobenzylamine |
| CN108892616A (en) * | 2018-08-31 | 2018-11-27 | 凯莱英生命科学技术(天津)有限公司 | Prepare continuous device and its application of benzaldehydes intermediate |
| CN108892616B (en) * | 2018-08-31 | 2024-06-07 | 凯莱英生命科学技术(天津)有限公司 | Continuous device for preparing benzaldehyde intermediate and application thereof |
| CN110963922B (en) * | 2018-09-30 | 2023-09-05 | 成都博腾药业有限公司 | Preparation method of 2,4, 6-trifluoro-benzylamine |
| CN110963922A (en) * | 2018-09-30 | 2020-04-07 | 成都博腾药业有限公司 | Preparation method of 2, 4, 6-trifluoro-benzene methylamine |
| CN110386864A (en) * | 2019-08-15 | 2019-10-29 | 天津凯莱英制药有限公司 | The method for continuously synthesizing of 2,4,6- trifluro benzaldehydes |
| CN111499540A (en) * | 2020-04-22 | 2020-08-07 | 中南民族大学 | Method for preparing 2,4,6-trichlorobenzonitrile by ammoxidation method, special catalyst and preparation method |
| CN111499540B (en) * | 2020-04-22 | 2022-09-27 | 中南民族大学 | Method for preparing 2,4,6-trichlorobenzonitrile by ammoxidation method, special catalyst and preparation method |
| CN114773147A (en) * | 2022-05-10 | 2022-07-22 | 浙江永太科技股份有限公司 | Preparation method of 2,4, 5-trifluorobenzyl bromide |
| CN115745766A (en) * | 2022-10-27 | 2023-03-07 | 兰州康鹏威耳化工有限公司 | Preparation method of trifluorobenzaldehyde and trifluorobenzyl bromide |
| CN115745766B (en) * | 2022-10-27 | 2024-05-14 | 兰州康鹏威耳化工有限公司 | Preparation method of trifluorobenzaldehyde and trifluorobenzyl bromide |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104610068B (en) | 2016-03-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104610068B (en) | A kind of preparation method of 2,4,6-trifluoro benzylamine compound | |
| CN105339352B (en) | The method that pyrazolecarboxamide is prepared for stereoselectivity | |
| CN103087019B (en) | Preparation method of tasimelteon | |
| CN103833560A (en) | Preparation method of (S)-5-chloro-alpha-cyclopropinyl-2-amino-alpha-trifluoromethyl phenylcarbinol | |
| CN105859553B (en) | A kind of preparation process of ethyl difluoro | |
| CN104341313A (en) | Synthesis of N,N,N'-trimethyl-N'-hydroxyethyl diethyl ether | |
| CN105503582A (en) | Continuous production method for trifluoro monochloro chrysanthemic acid | |
| CN104557760A (en) | Preparation method of aprepitant intermediate | |
| CN105273006B (en) | The preparation method of the tri isopropyl biphenyl of 2 dicyclohexylphosphontetrafluoroborate 2,4,6 | |
| CN102190574A (en) | Method for preparing 2-chloropropionyl chloride with high optical activity | |
| CN106365951B (en) | Prepare the recycling technique of 2- N-Propyl Bromide during 2,2- diisopropyl propionitrile | |
| CN101704724B (en) | Novel method for preparing high-proportion trans, trans-4-(4'-alkyl cyclohexyl) cyclohexyl alcohol liquid crystal intermediate compound | |
| CN103524305A (en) | Preparation method of 1,3-propanediol derivatives and intermediates | |
| CN104276979B (en) | The preparation method of agomelatine intermediate body | |
| CN107954882A (en) | A kind of preparation method of 2- amino -2- (the 4- tert-butyl group -2- ethoxyl phenenyls) ethanol | |
| CN104817444A (en) | Preparation method of anisyl propionaldehyde | |
| CN102964233A (en) | Synthetic method of 3,5-2-fluoro-(trifluoromethyl)benzophenone | |
| CN103467440B (en) | Synthesis method of 2-thiopheneethamine | |
| CN103772188B (en) | The preparation method of R-(+)-α-Cyclo hexyl mandelic acid | |
| CN105884629A (en) | N,N,N'-trimethyl-N'-aminopropyldiaminoethylether | |
| CN111548317A (en) | Efavirenz synthesis method and method for preparing intermediate thereof | |
| CN101210026A (en) | Method for preparing sodium tetraphenylborate | |
| CN104447562A (en) | New method for preparing dexmedetomidine hydrochloride key intermediate | |
| CN103694130A (en) | High-yield synthesis method of n-ethyl-p-menthane-3-carboxamide | |
| CN103086894A (en) | Synthesis method of electroplating additive 3-methyl-3-aminobutyne |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |