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A kind of synthetic method of 2,4-dichloro-5-fluorobenzoyl chloride

A technology of fluorobenzoyl chloride and synthesis method, which is applied in the field of synthesis of 2,4-dichloro-5-fluorobenzoyl chloride, and achieves the effects of convenient recovery and mechanical application, high catalytic reaction yield and lower reaction temperature

Active Publication Date: 2016-04-27
ZHEJIANG BENLI TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first step reaction uses granular AlCl 3 The yield is around 60%, although CCl 4 The amount used is more than 10 times that of 2,4-dichlorofluorobenzene, but there is still a relatively large proportion of dimer by-products (ie dichloro-bis(2,4-dichloro-5-fluorophenyl)methane) produced
Japanese patent JP4149143A uses mordenite / AlCl 3 As a catalyst, the yield of the first step was increased to 84.4%, but it failed to solve the problem of a large proportion of dimer by-products

Method used

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  • A kind of synthetic method of 2,4-dichloro-5-fluorobenzoyl chloride
  • A kind of synthetic method of 2,4-dichloro-5-fluorobenzoyl chloride
  • A kind of synthetic method of 2,4-dichloro-5-fluorobenzoyl chloride

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Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0032] 200 mL of SmCl with a concentration of 0.5 mol / L 3 and 100 mL of ZrOCl with a concentration of 0.5 mol / L 2 Place in a reaction vessel, add 200 mL of AlCl with a concentration of 0.5 mol / L under vigorous stirring 3 , and then slowly add concentrated ammonia water until the pH of the system is 9-10; after aging the reaction system at -18°C for 24 hours, suction filter and wash until there is no Cl - After detection, the filter cake was dried at 120°C, impregnated with 500mL ammonium persulfate solution with a concentration of 1mol / L for 4 hours, filtered, then dried, activated at 600°C for 3h to obtain 38g of solid acid catalyst S 2 o 8 2- / Sm 2 o 3 -ZrO 2 -Al 2 o 3 (ie catalyst Cat.1).

Embodiment 2-1

[0035] step 1)

[0036] Add 16.5 g (0.1 mol) of 2,4-dichlorofluorobenzene, CCl 4 15.4g (0.1mol), catalyst Cat. 10.83g and AlCl 3 33.3g (0.25mol), heat up to 40°C and stir for 4 hours. The hydrogen chloride produced by the reaction is absorbed by falling film. After the reaction, slowly inject the reactant into 50ml of distilled water, filter and recover the catalyst Cat.1, and the filtrate is separated. , the organic layer was washed with water, dried, and then distilled under reduced pressure to obtain 26.9 g of 2,4-dichloro-5-fluoro-(trichloromethyl)benzene with a yield of 95.2%.

[0037] step (2)

[0038] Add 26.9 g (0.095 mol) of 2,4-dichloro-5-fluoro-(trichloromethyl)benzene prepared in step (1) into the reaction flask, and then add FeCl 3 0.17g, heat up to 130°C, slowly add 1.8g (0.1mol) of distilled water dropwise under stirring conditions, drop it over 10 hours, and absorb the hydrogen chloride generated by the reaction with water. After the reaction, the reaction s...

Embodiment 2-2

[0040] step 1)

[0041] Add 16.5 g (0.1 mol) of 2,4-dichlorofluorobenzene, CCl 4 7.7g (0.05mol), catalyst Cat. 10.165g and AlCl 3 13.3g (0.1mol), heat up to 20°C and stir for 5 hours to react. The hydrogen chloride produced by the reaction is absorbed by falling film. After the reaction, slowly inject the reactant into 50ml of distilled water, filter and recover the catalyst Cat.1, and separate the filtrate , the organic layer was washed with water, dried, and then distilled under reduced pressure to obtain 13.1 g of 2,4-dichloro-5-fluoro-(trichloromethyl)benzene with a yield of 46.4%.

[0042] step (2)

[0043] Take 2,4-dichloro-5-fluoro-(trichloromethyl)benzene 28.3g (0.1mol) prepared by step (1) and add it to the reaction flask, then add FeCl 3 0.085g, heat up to 100°C, slowly add 1.8g (0.1mol) of distilled water dropwise under stirring conditions, drop it over 10 hours, absorb the hydrogen chloride generated by the reaction with water, after the reaction, the reaction s...

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Abstract

The invention discloses a method for synthesizing 2,4-dichloro-5-fluorobenzoyl. The method comprises the following steps: reacting 2,4-dichlor fluorbenzene and CCl4 serving as initial raw materials under actions of solid acid catalyst S2O82- / Sm2O3-ZrO2-Al2O3 and AlCl3 to generate 2,4-dichloro-5-fluoro-(trichloromethyl) benzene, and catalyzing and hydrolyzing by FeCl3. The method has the advantages that: the solid acid catalyst S2O82- / Sm2O3-ZrO2-Al2O3 can be conveniently recycled, the yield is high, so that the proportion of biopolymer byproducts can be reduced; use of high-pollution high-risk raw materials can be avoided, the operation safety is high, and pollutant emission is little; and the method can be used for breaking through the technical bottleneck of the reaction of aryl halide and CCl4, and massively consuming CCl4 which destroys the ozone layer by introducing acyl chloride functional group on an aromatic ring by adopting the CCl4 as a raw material.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a synthesis method of 2,4-dichloro-5-fluorobenzoyl chloride. technical background [0002] 2,4-dichloro-5-fluorobenzoyl chloride is the preparation of specific antipsychotic drugs triflupiperidinol, trifluoropiperidinol, penfluridol and synthetic broad-spectrum antibiotics such as the third-generation quinolone antibacterial drug ciproza It is the main raw material of star-level quinolones, and can also be used for the identification of pesticides, insecticides and ovicides, as well as plastics and resins. 2,4-Dichloro-5-fluorobenzoyl chloride is also an important basic raw material for the synthesis of high-performance functional polymer new materials polyaryl ketones, polyaryl ketones are a class of semi-crystalline aromatic thermoplastic polymer engineering materials, because Its aromatic ring contains halogen elements, and has excellent thermal properties, mechanical proper...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C63/70C07C51/58
CPCC07C17/269C07C17/383C07C51/58C07C51/64C07C63/10C07C25/13
Inventor 吴政杰
Owner ZHEJIANG BENLI TECH CO LTD
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