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Synthetic method of transfluthrin intermediate

A technique of transfluthrin and a synthetic method, which is applied in chemical instruments and methods, preparation of hydroxyl compounds, preparation of organic compounds, etc., can solve problems such as low yield, achieve simple reaction, high yield, and mild reaction conditions Effect

Active Publication Date: 2021-08-24
ZHEJIANG ZHONGXIN FLUORIDE MATERIALS CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] In order to overcome the above-mentioned shortcomings, especially the low yield, the present invention proposes a synthetic method of a transfluthrin pharmaceutical intermediate, which has the advantages of easy-to-obtain raw materials, stable and mild reaction conditions in each step, and greatly improved yield. advantage

Method used

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  • Synthetic method of transfluthrin intermediate

Examples

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Effect test

Embodiment 1

[0048] A new synthetic method of a transfluthrin intermediate 2,3,5,6-tetrafluorobenzyl alcohol, the method consists of the following steps:

[0049] (1) Synthesis of 2,3,5,6-tetrafluorotrichloromethylbenzene

[0050] In a 500mL four-necked flask with a stirring rod, a reflux condenser, a thermometer and a constant pressure dropping funnel, 92.4g (0.6mol) of carbon tetrachloride, 20.2g (0.15mol) of aluminum chloride and 5.0 zeolite were charged. g, after heating to 70°C, 9 g (0.06 mol) of 2,3,5,6-tetrafluorobenzene was slowly added dropwise, and the dropwise addition was completed within 1 hour. After the dropwise addition, the constant temperature reaction was continued for 1 h, and 300 mL of ice water was added to the reaction system after cooling. After the solid was filtered out, the organic layer was separated, and the aqueous layer was extracted three times with 50 mL of carbon tetrachloride, and the organic layer was combined, washed with 5% aqueous sodium bicarbonate ...

Embodiment 2

[0058] A new synthetic method of a transfluthrin intermediate 2,3,5,6-tetrafluorobenzyl alcohol, the method consists of the following steps:

[0059] (1) Synthesis of 2,3,5,6-tetrafluorotrichloromethylbenzene

[0060] In a 500mL four-necked flask with a stirring rod, a reflux condenser, a thermometer and a constant pressure dropping funnel, 138.6g (0.9mol) of carbon tetrachloride, 20.2g (0.15mol) of aluminum chloride and 5.0 zeolite were charged. g, after heating to 70°C, 9 g (0.06 mol) of 2,3,5,6-tetrafluorobenzene was slowly added dropwise, and the dropwise addition was completed within 1 hour. After the dropwise addition, the constant temperature reaction was continued for 1 h, and 300 mL of ice water was added to the reaction system after cooling. After the solid was filtered out, the organic layer was separated, and the aqueous layer was extracted three times with 50 mL of carbon tetrachloride, and the organic layer was combined, washed with 5% aqueous sodium bicarbonate...

Embodiment 3

[0068] A new synthetic method of a transfluthrin intermediate 2,3,5,6-tetrafluorobenzyl alcohol, the method consists of the following steps:

[0069] (1) Synthesis of 2,3,5,6-tetrafluorotrichloromethylbenzene

[0070] In a 500mL four-necked flask with a stirring rod, a reflux condenser, a thermometer and a constant pressure dropping funnel, 46.2g (0.3mol) of carbon tetrachloride, 20.2g (0.15mol) of aluminum chloride and 5.0 zeolite were charged. g, after heating to 70°C, 9 g (0.06 mol) of 2,3,5,6-tetrafluorobenzene was slowly added dropwise, and the dropwise addition was completed within 1 hour. After the dropwise addition, the constant temperature reaction was continued for 1 h, and 300 mL of ice water was added to the reaction system after cooling. After the solid was filtered out, the organic layer was separated, and the aqueous layer was extracted three times with 50 mL of carbon tetrachloride, and the organic layer was combined, washed with 5% aqueous sodium bicarbonate ...

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Abstract

The invention discloses a synthetic method of a transfluthrin intermediate, and belongs to the technical field of chemical synthesis, the synthetic method is characterized by comprising the following steps: (1) taking 2, 3, 5, 6-tetrafluorobenzene as a raw material, and reacting with carbon tetrachloride to obtain 2, 3, 5, 6-tetrafluorotrichloromethyl benzene; (2) under the action of a composite catalyst, carrying out catalytic hydrolysis on the 2, 3, 5, 6-tetrafluorotrichloromethyl benzene to obtain 2, 3, 5, 6-tetrafluorobenzoyl chloride; (3) under the action of a catalyst, the 2, 3, 5, 6-tetrafluorobenzoyl chloride and hydrogen are subjected to a Rosenmonde reduction reaction, and 2, 3, 5, 6-tetrafluorobenzaldehyde is obtained; (4) carrying out catalytic hydrogenation reaction on the 2, 3, 5, 6-tetrafluorobenzaldehyde and hydrogen to obtain 2, 3, 5, 6-tetrafluorobenzyl alcohol; the method has the advantages of simple steps, high yield of each step and simple reaction; the reaction conditions of each step are mild, and the method has the advantages of low cost, high yield and easily available reaction conditions.

Description

technical field [0001] The invention designs a method for synthesizing an intermediate in the technical field of pesticides, and in particular relates to a method for synthesizing a transfluthrin intermediate. Background technique [0002] Transfluthrin, as a new variety of pyrethroid pesticides, is a highly efficient and safe product developed by Bayer in Germany under the background that pests developed varying degrees of resistance to most pyrethroid insecticides in the 1980s. , Hygienic pyrethroid insecticides with low toxicity. The chemical name of transfluthrin is 2,3,5,6-tetrafluorobenzyl(1R,3S)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid . At present, transfluthrin is mainly used as a raw material for various mosquito coils and anti-moth products in China. It is a pyrethroid insecticide with a very promising market. [0003] 2,3,5,6-Tetrafluorobenzyl alcohol is an important intermediate for the synthesis of transfluthrin, but its synthesis is rel...

Claims

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Application Information

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IPC IPC(8): C07C33/46C07C29/141
CPCC07C17/269C07C29/141C07C45/41C07C51/58C07C33/46C07C47/55C07C63/68C07C25/13
Inventor 袁其亮蒋栋栋竺坚飞黄炜宋彭飞施正军俞伟樑石永根陈寅镐王超
Owner ZHEJIANG ZHONGXIN FLUORIDE MATERIALS CO LTD
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