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Method for synthesizing 3-chloro-5-trifluoromethyl trifluoroacetophenone

A technology of trifluoromethyl trifluoroacetophenone and trifluoromethyl aniline, which is applied in the field of synthesizing 3-chloro-5-trifluoromethyl trifluoroacetophenone, can solve problems that have not been reported, and achieve Save production time and cost, easy to adjust the reaction conditions, simplify the post-processing effect

Pending Publication Date: 2021-11-12
SHANGHAI SINOFLUORO SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] But, about the synthesis of 3-chloro-5-trifluoromethyl trifluoroacetophenone, it is seldom seen in bibliographical information, especially, has the potential to be applicable to the technical route of large-scale industrial production (such as production cost is low), more It has not been reported, and urgently needs to be developed and researched

Method used

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  • Method for synthesizing 3-chloro-5-trifluoromethyl trifluoroacetophenone
  • Method for synthesizing 3-chloro-5-trifluoromethyl trifluoroacetophenone
  • Method for synthesizing 3-chloro-5-trifluoromethyl trifluoroacetophenone

Examples

Experimental program
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Effect test

Embodiment 1

[0074] (1) Synthesis of 4-bromo-2-chloro-6-trifluoromethylaniline

[0075] Add 200g of o-aminobenzotrifluoride (1eq), 1kg of dichloromethane and 0.1g of iron powder to a 2L three-necked flask with an exhaust gas absorbing device in sequence; start stirring, cool down to 0°C, and drop 144.7g into the three-necked flask Cold (about -15°C) bromine monochloride (1.01eq), control the internal temperature at 0-5°C, after 1-3h dropwise addition, then keep warm for 2h; then, naturally heat up to 25°C, keep warm for bromination reaction , gas phase monitoring of the reaction process of the raw material o-aminobenzotrifluoride in the bromination reaction, monitoring shows: the bromination reaction is carried out for 2h, and the reaction of the raw material o-aminobenzotrifluoride is completed.

[0076] After the completion of the o-aminobenzotrifluorotoluene reaction, add 169.2 g of sulfonyl chloride (1.01 eq) dropwise to the reaction solution at 25° C., control the internal temperature...

Embodiment 2

[0090] (1) Synthesis of 4-bromo-2-chloro-6-trifluoromethylaniline

[0091] Add 120 g of o-aminobenzobenzotrifluoride (1 eq), 800 g of acetonitrile and 0.1 g of aluminum trichloride to a 2 L three-necked flask in sequence, and start stirring.

[0092] Cool down to 0°C, add 117.1g of dibromohydantoin solid (0.55eq) in batches (3g each time, 2h for feeding), control the internal temperature at 0-5°C, keep warm for 4h after addition; then naturally raise the temperature to 25°C , heat preservation for bromination reaction, gas phase monitoring of the reaction process of the raw material o-aminobenzotrifluoride in the bromination reaction, monitoring shows: the bromination reaction is carried out for 5h, and the reaction of the raw material o-aminobenzotrifluoride is completed.

[0093] After the reaction of o-aminotrifluorotoluene is completed, continue to add 64g of TCCA solid (0.37eq) to the reaction solution in batches at 25°C (1g each time, 3h for feeding), control the interna...

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Abstract

The invention discloses a method for synthesizing 3-chloro-5-trifluoromethyl trifluoroacetophenone, which comprises the following steps of: first brominating and then chlorinating 2-aminotrifluoromethylbenzene to obtain 4-bromo-2-chloro-6-trifluoromethylaniline; diazotizing the 4-bromo-2-chloro-6-trifluoromethylaniline, and treating the diazotized 4-bromo-2-chloro-6-trifluoromethylaniline with hypophosphorous acid or ethanol to obtain a deaminated compound 1-bromo-3-chloro-5-(trifluoromethyl) benzene; and preparing a Grignard reagent from the 1-bromo-3-chloro-5-(trifluoromethyl) benzene by using magnesium chips, and carrying out a nucleophilic reaction on the Grignard reagent and an acylation reagent to obtain 3-chloro-5-trifluoromethyl trifluoroacetophenone. The initial raw material 2-aminotrifluoromethylbenzene used in the route is a common chemical with low price, the product obtained by the reaction in each step is good in purity and high in yield, the environmental pollution is relatively small, and the method is expected to be used for large-scale industrial production.

Description

technical field [0001] The invention relates to a pesticide (such as pest repellent) intermediate containing fluorine element, in particular to a synthesis method of fluorine-containing fine chemicals. Background technique [0002] Due to the unique properties of fluorine element, fluorine-containing compounds have excellent properties, and are more and more widely used in medicine, pesticides, materials, etc. However, my country has natural advantages in fluorine resources. Therefore, fluorine-containing fine chemicals as organic intermediates are gradually showing great growth potential. [0003] Afoxolaner, whose trade name is NexGard, is the first oral repellent for dogs that targets both ticks and fleas and was launched in China in August 2017 by Boehringer Ingelheim. Insect medicine. It belongs to the isoxazoline compound, and its principle of action is to inhibit the GABA chloride ion channel of arthropods, and then the nerves are highly excited and lead to death. ...

Claims

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Application Information

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IPC IPC(8): C07C45/00C07C49/80
CPCC07C209/74C07C17/35C07C45/00C07C211/52C07C25/13C07C49/80
Inventor 赵云闾肖波陈鹏飞刘陈阳刘杰
Owner SHANGHAI SINOFLUORO SCI
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