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Preparation method of 4-amino-2-trifluoromethyl benzonitrile

A technology of trifluoromethyl benzonitrile and trifluoromethyl benzoic acid, which is applied in the field of preparation of 4-amino-2-trifluoromethyl benzonitrile, can solve the problem of large environmental impact, health hazards of operators, and restrictions on industrialization application and other issues, to achieve the effect of less environmental damage, reduced safety risks, and easy handling

Active Publication Date: 2020-04-28
常州沃腾化工科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] In the above several methods, cyanide-cuprous cyanide is required for the introduction of cyano groups. Cyanide is a highly toxic substance, and industrial production will cause health hazards to operators. Waste residue or waste water produced during post-treatment contains Cyanide ion and heavy metal copper ion, the three wastes are difficult to dispose of, and have a great impact on the environment. These disadvantages limit its industrial application

Method used

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  • Preparation method of 4-amino-2-trifluoromethyl benzonitrile

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Embodiment 1

[0037] (1) Preparation of 4-fluoro-2-trifluoromethylbenzoic acid

[0038] In a 500ml four-neck round bottom flask, put 5.76g (0.24mol) of magnesium chips, 1 grain of iodine, and 50ml of tetrahydrofuran under the protection of nitrogen, and heat to about 50°C. Dissolve 48.6 grams (0.2mol) of 2-bromo-5-fluorobenzotrifluoride in 200 milliliters of tetrahydrofuran, first drop about 10 milliliters into the reaction bottle, keep stirring until the color of iodine dissipates, confirm that the reaction is initiated, and then put it in a water bath Under cooling, the remaining material was slowly added dropwise, and after the drop was completed, the mixture was incubated for 1 hour to obtain the Grignard reagent.

[0039] The Grignard reagent was cooled to 5°C with ice water, and 21 g (0.47mol) of carbon dioxide was slowly introduced, then slowly raised to 25°C and kept stirring for 2 hours, then added 88 ml of hydrochloric acid (6Mol / L), stirred for half an hour, and separated into la...

Embodiment 2

[0048] (1) Preparation of 4-fluoro-2-trifluoromethylbenzoic acid

[0049] In a 500ml four-neck round bottom flask, put 6.24g (0.26mol) of magnesium chips, 1 grain of iodine, and 50ml of 2-methyltetrahydrofuran under the protection of nitrogen, and heat to about 50°C. Dissolve 48.6 grams (0.2mol) of 2-bromo-5-fluorobenzotrifluoride in 200 milliliters of 2-methyltetrahydrofuran, first drop about 10 milliliters into the reaction flask, keep stirring until the color of iodine dissipates, and confirm the initiation After the reaction, under cooling in a water bath, the remaining material was slowly added dropwise, and after the drop was completed, the mixture was incubated for 1 hour to obtain the Grignard reagent.

[0050] The Grignard reagent was cooled to 8° C. with ice water, and 26.4 grams (0.6 mol) of carbon dioxide was slowly introduced, then slowly raised to 30° C. and kept stirring for 2 hours, then 88 milliliters of hydrochloric acid (6Mol / L) was added, stirred for half a...

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Abstract

The invention relates to the technical field of chemical engineering, in particular to a preparation method of 4-amino-2-trifluoromethyl benzonitrile, which comprises the following steps: after 2-bromo-5-fluorobenzotrifluoride is subjected to a Grignard reaction, feeding carbon dioxide, and hydrolyzing to obtain 4-fluoro-2-trifluoromethyl benzoic acid; adding the 4-fluoro-2-trifluoromethyl benzoicacid into a pressure kettle, feeding liquid ammonia, and reacting under the action of a catalyst to generate 4-amino-2-trifluoromethyl benzamide; heating and dehydrating the 4-amino-2-trifluoromethylbenzamide with a dehydrating agent to generate the 4-amino-2-trifluoromethyl benzonitrile. According to the preparation method, highly toxic cuprous cyanide is not adopted, so that the safety risk ofproduction is reduced, and three wastes do not contain cyanide ions or a large amount of copper ions, are easier to treat and have small harm to the environment.

Description

technical field [0001] The invention relates to the technical field of chemical industry, in particular to a preparation method of 4-amino-2-trifluoromethylbenzonitrile. Background technique [0002] 4-amino-2-trifluoromethylbenzonitrile (3-trifluoromethyl-4-cyanoaniline) is a key intermediate for the preparation of anti-prostate cancer drugs bicalutamide and enzalutamide, and its preparation method is currently There are mainly the following types: [0003] Bioorganic and Medicinal Chemistry Letters1998.8 (7) p.745-750 reported the route with 3-trifluoromethylacetanilide as raw material: [0004] [0005] Specifically, 3-trifluoromethylacetanilide undergoes bromination, hydrolysis deprotection, and cyanation to obtain 4-amino-2-trifluoromethylbenzonitrile. [0006] The Chinese invention patent with the publication number CN1810775B discloses a process route using m-fluorobenzotrifluoride as a raw material: [0007] [0008] Specifically, 4-amino-2-trifluoromethylbe...

Claims

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Application Information

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IPC IPC(8): C07C253/20C07C255/58
CPCC07C253/20C07C231/14C07C51/15C07C255/58C07C237/40C07C63/70Y02P20/141
Inventor 李红功
Owner 常州沃腾化工科技有限公司
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