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Preparation method and intermediate of 1-(3,5-dichloro-4-fluorophenyl)-2,2,2-trifluoroethyl ketone

A technology of trifluoroethyl ketone and phenyl, which is applied in the application field of synthetic chemistry, can solve the problems of high equipment requirements, difficult industrialization, and many impurities, and achieve the effect of industrialized production, good purity and yield, and simple preparation process

Active Publication Date: 2020-12-22
ZHEJIANG YONGTAI TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] WO2017201134 discloses that 1-(3,5-dichloro-4-fluoro-phenyl)-2 ,2,2-Trifluoroethanone, because the reaction involves Grignard reaction, the Grignard reaction solution is easy to self-coupling, resulting in low yield, many impurities, and poor effect, which is not conducive to industrial production, and the Grignard reaction High requirements for industrial equipment lead to high production costs; in addition, there are related studies using fluorobenzene as raw material, first through Friedel-Crafts reaction, then nitration, chlorination, and then free radical chlorination to obtain 1-(3,5- Dichloro-4-fluoro-phenyl)-2,2,2-trifluoroethanone, the reaction cost is low, but free radical chlorination needs to be reacted at higher than 180°C, and under acidic conditions, it will corrode the equipment Very strong, resulting in difficulties in industrialization

Method used

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  • Preparation method and intermediate of 1-(3,5-dichloro-4-fluorophenyl)-2,2,2-trifluoroethyl ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1: Preparation of 2-fluoro-3-chloro-5-trifluoroacetylaniline

[0037]

[0038] 1.1

[0039] Put 271.5g (1mol) 2-fluoro-3-chloro-5-trifluoroacetylnitrobenzene, 900g methanol, and 5g platinum carbon into a 2L autoclave, close the autoclave, raise the temperature to 50°C, and let the pressure of hydrogen flow to 1- 2MPa, heat preservation for 8h, sampling control, the reaction is completed, cooled to room temperature, filtered and concentrated to obtain 225g of 2-fluoro-3-chloro-5-trifluoroacetylaniline with a purity of 95.5% and a yield of 93.2%.

[0040] 1.2

[0041] Different from Example 1.1, the present example replaces methanol with ethyl acetate, and all the others are the same, the steps are as follows:

[0042] Put 271.5g (1mol) 2-fluoro-3-chloro-5-trifluoroacetylnitrobenzene, 900g ethyl acetate, and 5g platinum carbon into a 2L autoclave, close the autoclave, raise the temperature to 50°C, and let the pressure of hydrogen flow to 1 -2MPa, heat prese...

Embodiment 2

[0056] Example 2: Preparation of 1-(3,5-dichloro-4-fluoro-phenyl)-2,2,2-trifluoroethanone

[0057]

[0058] 2.1

[0059] Put 327g (2.5mol) of 75% sulfuric acid into a 1L four-necked bottle, and add 121g (0.5mol) of 2-fluoro-3-chloro-5-trifluoroacetylaniline prepared according to the method in Example 1.1 at 45°C, and then drop Add 190.5g (0.6mol) of 40% nitrosylsulfuric acid, keep it warm for 1 hour to obtain diazonium solution, put 182.5g (1.5mol) of hydrochloric acid and 30g of cuprous chloride into another 1L four-necked bottle, and heat up to 40-50 ℃, add heavy nitrogen solution dropwise, keep warm for 2 hours after dropping, let stand to separate layers, extract with acid layer, combine oil layers, wash with water, wash with alkali, separate layers, concentrate, and rectify to obtain 1-(3,5-dichloro-4-fluoro -Phenyl)-2,2,2-trifluoroethanone 107g, purity 99%, yield 82%.

[0060] 2.2

[0061] Different from Example 2.1, the amount of nitrosyl sulfuric acid in this exa...

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Abstract

The invention discloses a preparation method and an intermediate of 1-(3,5-dichloro-4-fluorophenyl)-2,2,2-trifluoroethyl ketone, and relates to the technical field of synthetic chemical application. The method comprises the following steps: (1) by taking a compound I as a raw material, carrying out hydrogenation reduction under the action of a solvent and a catalyst to obtain a compound II; and (2) carrying out diazo reaction on the compound II and a diazo reagent under the action of an acid, and then carrying out chlorination reaction under the action of hydrochloric acid and a catalyst to obtain a compound III, so as to achieve simple and efficient preparation of the compound 1-(3,5-dichloro-4-fluorophenyl)-2,2,2-trifluoroethyl ketone with high purity and good yield.

Description

technical field [0001] The invention relates to the technical field of synthetic chemistry application, in particular to a preparation method and an intermediate of 1-(3,5-dichloro-4-fluoro-phenyl)-2,2,2-trifluoroethanone. Background technique [0002] 1-(3,5-dichloro-4-fluoro-phenyl)-2,2,2-trifluoroethanone is an important intermediate for the preparation of isoxazoline-substituted benzamides, whose chemical formula is as follows Shown: [0003] [0004] It is disclosed in EP1932836Al that isoxazoline benzamide compounds have the activity of killing harmful organisms; Application in the preparation of bactericides or antibacterial agents and in the preparation of FtsZ inhibitor drugs, as an important intermediate for the preparation of isoxazoline-substituted benzamides, 1-(3,5-dichloro-4-fluoro-benzene base)-2,2,2-trifluoroethanone has a good market demand. [0005] WO2017201134 discloses that 1-(3,5-dichloro-4-fluoro-phenyl)-2 ,2,2-Trifluoroethanone, because the re...

Claims

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Application Information

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IPC IPC(8): C07C45/63C07C49/80C07C221/00C07C225/22
CPCC07C45/63C07C221/00C07C225/22C07C49/80
Inventor 邵鸿鸣李飞陈少亭柴恩德孙震
Owner ZHEJIANG YONGTAI TECH CO LTD
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