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The synthetic method of flubenzuron intermediate 2-fluoro-4-(2-chloro-4-trifluoromethylphenoxy) aniline

A technology of trifluoromethylphenoxy and synthesis method is applied in the synthesis field of insect growth regulator flufenoxuron intermediate 2-fluoro-4-aniline, and can solve the problem of low content, unfavorable industrial production and low product yield and other problems, to achieve the effect of high product content, low raw material price and high total yield

Active Publication Date: 2017-11-24
JIANGSU FLAG CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Although this synthetic route has few reaction steps and moderate conditions, the yield reported in the literature is only 37%, the product yield is low, and the content is low, which is not conducive to large-scale industrial production

Method used

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  • The synthetic method of flubenzuron intermediate 2-fluoro-4-(2-chloro-4-trifluoromethylphenoxy) aniline
  • The synthetic method of flubenzuron intermediate 2-fluoro-4-(2-chloro-4-trifluoromethylphenoxy) aniline
  • The synthetic method of flubenzuron intermediate 2-fluoro-4-(2-chloro-4-trifluoromethylphenoxy) aniline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 39.7 g (0.3 mol) of 3-fluoro-4-aminophenol and 158.8 g of dichloroethane into a 250 ml four-necked flask equipped with a thermometer, a stirrer, and a cooling device, and stir to cool down to (10-20) °C. Control the temperature (10-20) ℃ and add 34 g (0.33 mol) of acetic anhydride dropwise for about 30 minutes. During the dropping process, the exotherm is violent. Keep the temperature at (10-20) ℃ for 2 hours until the reaction of the HPLC raw materials is completed. Control temperature (10-20) ℃ and add 30% sodium hydroxide aqueous solution dropwise to pH (5-6), filter, wash with 40 grams of water, and dry to obtain 49.6 grams of brown solid, content 97.9%, yield: 95.8%

Embodiment 2

[0027] Add 39.7 g (0.3 mol) of 3-fluoro-4-aminophenol and 158.8 g of dichloroethane into a 250 ml four-necked flask equipped with a thermometer, a stirrer, and a cooling device, and stir to cool down to (10-20) °C. Add 43.3 g (0.33 moles) of propionic anhydride dropwise under temperature control (10-20) °C, and drop it in about 30 minutes. During the dropping process, the exotherm is violent, and keep warm at (10-20) °C for 2 hours until the reaction of the HPLC raw materials is completed. Control temperature (10-20) ℃ and add 30% sodium hydroxide aqueous solution dropwise to pH (5-6), filter, wash with 40 grams of water, and dry to obtain 51.8 grams of brown solid, content 95.2%, yield: 89.8%

[0028] Preparation of Intermediate II 2-fluoro-4-(2-chloro-4-trifluoromethylphenoxy)acetanilide

Embodiment 3

[0030] Under nitrogen protection, DMSO 265 grams, potassium hydroxide 18.8 grams (0.333 moles), 3-fluoro-4-acetamidophenol Heat and stir 52.3 grams (0.303 moles) to (60-70) ℃ and keep it warm for 0.5 hours, then steam out about 30 grams of solvent with high vacuum (the measured water content is basically anhydrous), and the reaction liquid in the kettle is qualified if the water content is less than 1%. Afterwards, fill the air with nitrogen and add 72.3 g (0.333 moles) of 3.4-dichlorobenzotrifluoride at (60-70) ° C, continue to stir and heat to (110-120) ° C and keep it warm for 4 hours, and the HPLC raw material is reacted to <0.5% is qualified. After passing the test, cool down to (50-60)°C with negative pressure and high positive space to distill the solvent DMSO, evaporate about 80% and add 200 grams of water dropwise at (50-60)°C to produce a large amount of dark brown solid, filter 60 grams of water to wash Drained and dried to obtain 104.2 grams of dark brown solid, w...

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Abstract

The invention discloses a flufenoxuron intermediate 2-fluoro-4-(2-chloro-4- trifluoromethyl phenoxyl) aniline synthesis method comprising the following steps: A) preparing 3-fluoro-4-acetyl amino phenol by acylation reaction of 3-fluoro-4-aminophenol and an organic acid anhydride; B) preparing 2-fluoro-4-(2-chloro-4- trifluoromethyl phenoxyl) acetanilide by condensation reaction of the 3-fluoro-4-acetyl amino phenol and 3, 4-dichloro trifluoromethyl benzene in a polar solvent and in the presence of an alkaline compound; C) preparing the 2-fluoro-4-(2-chloro-4- trifluoromethyl phenoxyl) aniline by acidolysis and alkali neutralization reaction of the 2-fluoro-4-(2-chloro-4- trifluoromethyl phenoxyl) acetanilide. The flufenoxuron intermediate 2-fluoro-4-(2-chloro-4- trifluoromethyl phenoxyl) aniline synthesis method has the advantages of mild reaction conditions, simple technological operation process, low-price and easy-to-get raw materials, simple reaction, short synthetic route, high total yield, high product content, low production cost, and the like, has less production of "three wastes", and is suitable for industrial scale production.

Description

technical field [0001] The invention belongs to the field of chemical industry, and in particular relates to a new method for synthesizing 2-fluoro-4-(2-chloro-4-trifluoromethylphenoxy)aniline, an intermediate of the insect growth regulator flubenzuron. Background technique [0002] 2-Fluoro-4-(2-chloro-4-trifluoromethylphenoxy)aniline is an important intermediate of insect growth regulator fiflubenzuron. [0003] Flubenzuron is a benzoylurea insecticide and acaricide developed by Shell. It is mainly used to control pests and mites on apples, citrus and other fruit trees, vegetables, cotton and other plants. , Rust mites (rust spiders), leaf miners, diamondback moths, cabbage caterpillars, cotton bollworms, core-eating insects, noctuids and locusts all have good control effects. Chinese aliases of flubenzuron: Flufenuron, 1-[2-fluoro-4-(2-chloro-4-trifluoromethylphenoxy)phenyl]-3-(2,6-difluorobenzyl Acyl)urea, English name: flufenoxuron, CAS number: 101463-69-8, molecular ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C213/08C07C217/90
Inventor 王正旭王凤云吴耀军
Owner JIANGSU FLAG CHEM IND