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Preparation method of halogenated trifluoroacetyl benzene

A technology of trifluoroacetyl and trichlorotrifluoroacetyl is applied in the preparation of halogenated hydrocarbons, the preparation of organic compounds, the preparation of carbon-based compounds, etc., and can solve complex production operations, low product yield and purity, and few synthesis methods. question

Active Publication Date: 2021-06-01
SHANGHAI CHEMSPEC CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few synthetic methods reported in existing literature on this type of compound, and there are deficiencies such as expensive raw materials, complicated production operations, and low product yield and purity.

Method used

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  • Preparation method of halogenated trifluoroacetyl benzene
  • Preparation method of halogenated trifluoroacetyl benzene
  • Preparation method of halogenated trifluoroacetyl benzene

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preparation example Construction

[0050] The first aspect of the present invention provides a method for preparing 3,4,5-trichlorotrifluoroacetophenone, comprising:

[0051] 1) Diazotization and chlorination of 2,6-dichloro-4-bromoaniline to provide 3,4,5-trichlorobromobenzene;

[0052] 2) 3,4,5-trichlorobromobenzene is subjected to a Grignard reaction to provide 3,4,5-trichlorophenylmagnesium bromide;

[0053] 3) Trifluoroacetylation of 3,4,5-trichlorophenylmagnesium bromide with a trifluoroacetylating reagent to provide 3,4,5-trichlorotrifluoroacetophenone.

[0054] The preparation method of 3,4,5-trichlorotrifluoroacetophenone provided by the present invention may comprise: performing a trifluoroacetylation reaction with 3,4,5-trichlorophenylmagnesium bromide and a trifluoroacetylating reagent , to provide 3,4,5-trichlorotrifluoroacetophenone.

[0055] In the above trifluoroacetylation reaction, the trifluoroacetylating reagent may specifically be one or more combinations of trifluoroacetyldiethylamine, e...

Embodiment 1

[0093] Diazotization, chlorination reaction

[0094] Put 2,6-dichloro-4-bromoaniline (2.4kg, 9.96mol), 30% hydrochloric acid (6kg), water (1kg) into a 20L four-necked flask, start stirring, heat and control the internal temperature to 90-95°C for reaction 1 Hours, cool naturally, add dropwise sodium nitrite aqueous solution (0.76kg sodium nitrite dissolved in 2.4kg water) at an internal temperature of -5 to 0°C, and keep at an internal temperature of -5 to 0°C for 0.5 hours. A solution of the diazonium salt was obtained.

[0095] Take another 20L four-necked flask, put in cuprous chloride (0.4kg, 0.167mol), 30% hydrochloric acid (3.2kg), control the internal temperature at 60-65°C and add the previously prepared diazonium salt solution dropwise, and control the internal temperature at 60-60°C. Continue to keep warm at 65°C for 0.5 hours.

[0096] After the reaction was completed, dichloroethane (4.8 kg) was added, and layers were stirred, the organic layer was washed with wa...

Embodiment 2

[0099] Diazotization, chlorination reaction

[0100] 20L four-neck flask, put 2,6-dichloro-4-bromoaniline (2.4kg, 9.96mol), 30% hydrochloric acid (3kg), toluene (2.5Kg), water (1kg), start stirring, heat and control the internal temperature React at 90-95°C for 1 hour, cool naturally, add tert-butyl nitrite (1232.5g, 11.95mol) dropwise at an internal temperature of -5-0°C, and keep at an internal temperature of 15-20°C for 0.5 hours. A solution of the diazonium salt was obtained.

[0101] Take another 20L four-necked flask, put in cuprous oxide (0.4kg, 0.167mol), 30% hydrochloric acid (3.2kg), control the internal temperature at 60-65°C, add the previously prepared diazonium salt solution dropwise, and control the internal temperature at 60-65°C. °C for 0.5 hours.

[0102] After the reaction, add toluene (4.8kg), stir and separate layers, wash the organic layer with water, separate the water layer, and precipitate the organic layer to obtain 2.5kg of oil.

[0103] The oil w...

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Abstract

The invention relates to the field of organic synthesis, in particular to a preparation method of halogenated trifluoroacetyl benzene. The invention provides a preparation method of 3,4,5-trichlorotrifluoroacetyl benzene on the first aspect, which comprises the following steps: 1) carrying out diazotization and chlorination reaction on 2,6-dichloro-4-bromoaniline to provide 3,4,5-trichlorobromobenzene; (2) carrying out Grignard reaction on the 3,4,5-trichlorobromobenzene so as to provide 3,4,5-trichlorophenyl magnesium bromide; and 3) carrying out a trifluoroacetylation reaction on the 3,4,5-trichlorophenyl magnesium bromide and a trifluoroacetylation reagent, so as to provide the 3,4,5-trichlorotrifluoroacetyl benzene. According to the preparation method of 3,4,5-trichlorotrifluoroacetyl benzene, provided by the invention, 2,6-dichloro-4-bromoaniline is adopted as a raw material, a target product is prepared through a diazotization reaction, a Grignard reaction and a trifluoroacetylation reaction, the whole preparation route is simple in reaction step operation, the product is easy to purify, the yield is high, and the preparation method is very suitable for large-scale production; and the method has a good industrialization prospect.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of halogenated trifluoroacetophenone. Background technique [0002] Halogen-substituted trifluoroacetophenones are commonly used chemical intermediates, and these compounds often have a very wide range of uses, such as 3,5-dichloro-4-fluorotrifluoroacetophenone, etc. However, there are few synthetic methods reported in the existing literature on this type of compound, and there are disadvantages such as expensive raw materials, complicated production operations, and low product yield and purity. Contents of the invention [0003] In view of the above-mentioned shortcomings of the prior art, the object of the present invention is to provide a preparation method of halogenated trifluoroacetophenones, which is used to solve the problems in the prior art. [0004] In order to achieve the above purpose and other related purposes, the present invention provides ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/80C07C45/45C07C45/63
CPCC07C45/455C07C45/63C07F3/02C07C17/093C07C245/20C07C49/80C07C25/02
Inventor 李晓亮何立顾竞杨建华
Owner SHANGHAI CHEMSPEC CORP
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