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A method for preparing 1-(2-chlorophenyl)-2-(4-fluorophenyl) propylene

A technology of fluorophenyl and chlorophenyl, which is applied in the field of preparing 1--2-propene, can solve problems such as unsatisfactory product yield and quality, improve equipment production capacity, reduce environmental impact, and reduce raw materials cost effect

Active Publication Date: 2014-08-06
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the product yield and quality obtained by the preparation method disclosed in the description are all unsatisfactory

Method used

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  • A method for preparing 1-(2-chlorophenyl)-2-(4-fluorophenyl) propylene

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Experimental program
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Effect test

Embodiment 1

[0021] Add 161g (1mol) of o-chlorobenzyl chloride and 249g (1.5mol) of triethyl phosphonite into a 500ml three-neck flask, raise the temperature to reflux, and continue to reflux, the temperature rises to 170-180°C, and react for 12 hours (sampling and analysis When the chlorobenzyl chloride reaction is completed), excess triethyl phosphinate was removed under reduced pressure to obtain 255 g of diethyl o-chlorobenzyl phosphonate with a content of 95% and a yield of 97%.

Embodiment 2

[0023] Add 161g (1mol) of o-chlorobenzyl chloride and 186g (1.5mol) of trimethyl phosphinate into a 500ml three-necked flask, raise the temperature to reflux, and continue to reflux, the temperature rises to 170-180°C, and react for 12 hours (sampling and analysis When the chlorobenzyl chloride reaction is completed), excess trimethyl phosphinate was removed under reduced pressure to obtain 218 g of dimethyl o-chlorobenzyl phosphonate with a content of 95.5% and a yield of 97%.

Embodiment 3

[0025] Add 218g (3.9mol) of potassium hydroxide, 1000ml of toluene, and 95g of DMF into a 2000ml three-neck flask, and add diethyl o-chlorobenzylphosphonate 349 (1.33mol) and p-fluorobenzene under stirring. Ethyl ketone 180g (1.3mol, content 98%) was stirred and reacted at 20-30° C. for 12 hours. Gas chromatography followed the completion of the reaction. Added 400ml of water, stirred, and separated into layers. After the solvent was distilled off from the organic layer under reduced pressure, 305 g of 1-(o-chlorobenzyl)-2-(4-fluorophenyl)-1-propene was obtained, with a content of 96% and a yield of 95%.

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Abstract

The invention belongs to organic synthesis field, discloses a method for preparing 1-(2-chlorophenyl)-2-(4-fluorophenyl) propylene, comprises the following reaction steps that: (1). 2-chlorobenzylphosphodiester is prepared by the stirring reaction of 2-cyanobenzylchloride and sulphite under backflow state; (2). 1-(2- chlorophenyl)-2-(4- fluorophenyl) propylene is prepared by the reaction of 2-chlorobenzylphosphodiester and 4-fluoroacetophenone; wherein, the step 2 uses N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, N-methyl pyrrolidone, 1,4-dioxane or acetonitrile and other polar solvent as the catalyst and undergoes reaction under highly basic condition. The preparation method of the invention has advantages of simple operation, mild condition, adequate product quality and high yield, and is suitable for industrialization popularization and application.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a method for preparing 1-(2-chlorophenyl)-2-(4-fluorophenyl)propene. Background technique [0002] Epoxiconazole (trade name Ouba) is a broad-spectrum fungicide with preventive and therapeutic effects developed by BASF in 1983. It not only has good protection, treatment and eradication activities, but also has systemic and better It is widely used in commercial crops and can control almost all fungal diseases. [0003] The production of epoxiconazole mainly adopts the synthetic method reported in US Patent No. 50812317A. Grignard reagent is used in the reaction process of this method, and a large amount of hydrogen gas is released during the reaction process, which has relatively high safety requirements for the workshop. A new synthetic route is disclosed in Chinese patent application CN101513183A, and 1-(2-chlorophenyl)-2-(4-fluorophenyl)propene is an important intermediate in th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C25/24C07C17/26B01J31/02
Inventor 吴公信周银平白丽萍梁敏孙克
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD