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New synthetic method of pesticide fludioxonil intermediate

A technology for fludioxonil and intermediates, which is applied in the new synthesis field of pesticide fludioxonil intermediates, can solve the problems of serious pollution of three wastes, poor comprehensive benefits, long cycle, etc., and achieve the effect of simple operation, convenient treatment and simple steps

Inactive Publication Date: 2014-07-02
SUZHOU VIVOTIDE BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The process has many steps, a long cycle, uses highly toxic raw materials, serious pollution of three wastes, high cost, and poor comprehensive benefits

Method used

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  • New synthetic method of pesticide fludioxonil intermediate
  • New synthetic method of pesticide fludioxonil intermediate
  • New synthetic method of pesticide fludioxonil intermediate

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preparation example Construction

[0023] The new synthetic method of pesticide fludioxonil intermediate comprises the following steps:

[0024] Step 1) adding triphenylphosphine to the toluene solution of bromoacetonitrile, and after reflux reaction for 4 hours, filter to obtain bromoacetonitrile triphenylphosphine salt white solid;

[0025] Step 2) At low temperature, slowly dropwise add a cyclohexane solution of n-butyllithium into the tetrahydrofuran solution of 2,2-difluoro-1,3-benzodioxol, react for 1 hour, then slowly add N , N-dimethylformamide, then reacted for 30 minutes, then slowly warmed up to room temperature, after 30 minutes, quenched the reaction with 2mol / L hydrochloric acid solution, extracted with ethyl acetate, washed the organic layer with saturated saline, and anhydrous sulfuric acid Drying over sodium and evaporating the solvent gave 4-formyl-2,2-difluoro-1,3-benzodioxol;

[0026] Step 3) Dissolve 4-formyl-2,2-difluoro-1,3-benzodioxol and bromoacetonitrile triphenylphosphonium salt in d...

Embodiment 1

[0030] Step 1) 10 grams of bromoacetonitrile was added to 300 milliliters of toluene, then 21.8 grams of triphenylphosphine was added, and after reflux reaction for 4 hours, the white precipitate was filtered to obtain 30.5 grams of bromoacetonitrile triphenylphosphonium salt;

[0031] Step 2) 15.8 grams of 2,2-difluoro-1,3-benzodioxol was added to 200ml of dry tetrahydrofuran, cooled to -75°C under nitrogen protection, and then slowly added dropwise into 6.4 grams of n-butyllithium After reacting for 1 hour, slowly add 7.31 g of N,N-dimethylformamide dropwise, react for 30 minutes after the drop, then slowly warm up to room temperature, after 30 minutes, use 2mol / L hydrochloric acid The reaction was quenched by the solution, extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated to obtain 16.5 g of 4-formyl-2,2-difluoro-1,3-benzodioxol;

[0032] Step 3) Dissolve 10 grams of 4-formyl...

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Abstract

The invention discloses a new synthetic method of a pesticide fludioxonil intermediate. The method comprises the steps of firstly preparing bromoacetonitrile triphenyl phosphate white solid; then preparing 4-formyl-2,2-difluoro-1,3-benzodioxole; finally dissolving 4-formyl-2,2-difluoro-1,3-benzodioxole and bromoacetonitrile triphenyl phosphate into dichloromethane at room temperature, dropping a small amount of a 10% sodium hydroxide solution, and reacting to obtain (E)-3-(2,2-difluoro-1,3-benzodioxolame-4-yl) acrylonitrile. By adopting the method disclosed by the invention, the technical problems that an original synthetic method is more in steps, long in period, relatively highly-toxic in raw materials, serious in three-waste pollution and high in cost are solved.

Description

technical field [0001] The invention relates to a chemical synthesis method, in particular to a novel synthesis method of a pesticide fludioxonil intermediate. Background technique [0002] The trade name of fludioxonil is Shilax, which is a new type, high-efficiency and safe fungicide, and is currently one of the largest-selling seed treatment agents in the world. Because of its small dosage and long duration, it is rated as a zero-risk product by the U.S. Environmental Protection Agency and has an extremely broad market prospect. Fludioxonil is a systemic broad-spectrum fungicide, which can be used as a foliar fungicide to control Fusarium nivalophilus, Ticky black rot, etc., especially effective against Botrytis cinerea. Rhyclonil is mainly used as a seed treatment agent for cereal and non-cereal crops. [0003] At present, the route of synthesizing (E)-3-(2,2-difluoro-1,3-benzodioxolan-4-yl)acrylonitrile is as follows: [0004] [0005] a. Reaction of 2,2-difluoro-...

Claims

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Application Information

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IPC IPC(8): C07D317/46
CPCC07D317/46
Inventor 凌静张冬冬
Owner SUZHOU VIVOTIDE BIOTECH
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