Preparation method of compound 2,4,6-trifluorobenzylamine

A technology of trifluorobenzylamine and compounds, which is applied in the preparation of organic compounds, the preparation of amino compounds, chemical instruments and methods, etc., can solve the problems of low yield, difficult recovery and application, and many hydrogenation reaction by-products, etc. The effect of high yield, low cost of raw materials and short reaction steps

Active Publication Date: 2021-03-09
浙江丽晶化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the method has short reaction steps and cheap raw materials, the catalyst palladium carbon used in the two-step hydrogenation reaction is expensive and difficult to recycle and apply mechanically. At the same time, there are many by-products in the hydrogenation reaction and the yield is low, resulting in low industrial production benefits.

Method used

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  • Preparation method of compound 2,4,6-trifluorobenzylamine
  • Preparation method of compound 2,4,6-trifluorobenzylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] In a 2000ml three-necked flask, add 200g of pentachlorobenzonitrile (0.726mol), 160g of anhydrous potassium fluoride (2.75mol), and 1000g of sulfolane, stir, and under nitrogen protection, add 6.0g of 18-crown-6 and heat up to 125 ℃-135℃ reflux reaction for 4h. After the reaction is complete, lower the temperature to below 50°C, filter, add 2000ml of water and 800ml of cyclohexane to the filtrate, stir, separate layers, take the organic layer and wash it with 400ml water, separate layers, dry with anhydrous sodium sulfate, filter, and evaporate the filtrate under reduced pressure. The solvent was removed to obtain 154.8 g of 3,5-dichloro-2,4,6-trifluorobenzonitrile (yield 94.3%, HPLC purity 98.7%).

Embodiment 2

[0034] Add 20g of 3,5-dichloro-2,4,6-trifluorobenzonitrile (0.0885mol), 300g of water, 23.2g of zinc powder (0.355mol) into a 500ml three-necked flask, stir, raise the temperature to 90°C, and add dropwise 43.1 A mixture of 30% concentrated hydrochloric acid (0.355mol) and 80g acetic acid (1.332mol) (mixed acid molar ratio 1:3.8), added dropwise for 2 hours, then kept at 95°C-105°C for 4 hours, and cooled down to room temperature after the reaction was complete. Add 250ml of dichloromethane to stir, filter, the filtrate is layered, take the organic layer and adjust the pH to 7 with saturated aqueous sodium bicarbonate solution, then separate the layers, wash the organic layer with 150ml of water, dry over anhydrous magnesium sulfate, filter, and distill the filtrate under reduced pressure 11.0 g of 2,4,6-trifluorobenzonitrile was obtained (yield 79.1%, GC purity 97.2%).

Embodiment 3

[0036] Add 20g of 3,5-dichloro-2,4,6-trifluorobenzonitrile (0.0885mol), 300g of water, 23.2g of zinc powder (0.355mol) into a 500ml three-necked flask, stir, raise the temperature to 90°C, and add dropwise 43.1 A mixture of 30% concentrated hydrochloric acid (0.355mol) and 60g acetic acid (0.999mol) (mixed acid molar ratio 1:2.8), added dropwise for 2 hours, then kept at 95°C-105°C for 5 hours, and cooled down to room temperature after the reaction was complete. Add 250ml of dichloromethane and stir, filter, the filtrate is layered, take the organic layer and adjust the pH to 7 with saturated aqueous sodium bicarbonate solution, then separate the layers, wash the organic layer with 150ml of water, dry over anhydrous magnesium sulfate, filter, and distill the filtrate under reduced pressure 10.7 g of 2,4,6-trifluorobenzonitrile was obtained (yield 77.0%, GC purity 97.5%).

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Abstract

The invention discloses a preparation method of a compound 2,4,6-trifluorobenzylamine, and relates to the field of organic synthesis. According to the preparation method, pentachlorobenzonitrile is used as a starting raw material and is subjected to a fluorination reaction with a fluorinating agent in an organic solvent under the action of a catalyst to obtain 3,5-dichloro-2,4,6-trifluorobenzonitrile. The obtained 3,5-dichloro-2,4,6-trifluorobenzonitrile is added into water and reacts with zinc powder and mixed acid, and then reflux dechlorination is performed to obtain 2,4,6-trifluorobenzonitrile. The obtained 2,4,6-trifluorobenzonitrile is added into an organic solvent, and hydrogenation reduction is carried out under the action of an organic alkali and a catalyst to obtain the product 2,4,6-trifluorobenzylamine. The method has the advantages of short synthesis route, simple operation, mild reaction conditions, cheap and easily available raw materials and stable product quality, andis suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a method for preparing a pesticide and a pharmaceutical intermediate 2,4,6-trifluorobenzylamine, which belongs to the technical field of chemical engineering, and specifically relates to the field of chemical synthesis. Background technique [0002] 2,4,6-Trifluorobenzylamine is an important pesticide and pharmaceutical intermediate, which is widely used in drug synthesis and other fields, and is also a key intermediate for the synthesis of drug Bictegravir, with high market prospects and value. [0003] The synthetic method of disclosed 2,4,6-trifluorobenzylamine mainly contains following three kinds at present: [0004] ①Patent W09845268 discloses that 2-bromomethyl-1,3,5-trifluorobenzene is used as a starting material to form a salt with urotropine, and then hydrolyzed under acidic conditions to obtain 2,4,6-trifluorobenzylamine . The method raw material 2-bromomethyl-1,3,5-trifluorobenzene is relatively difficult to obtai...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/48C07C211/29C07C253/30C07C255/50
CPCC07C253/30C07C209/48C07C255/50C07C211/29
Inventor 颜国和王祥祥
Owner 浙江丽晶化学有限公司
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