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Method for preparing epoxiconazole intermediate

The technology of an intermediate and epoxiconazole, which is applied in the field of preparation of epoxiconazole intermediates, can solve the problems of low content and yield, complicated operation and high cost, and achieves high content and yield, simple process and less three wastes. Effect

Active Publication Date: 2012-01-04
JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method is complicated to operate, and the conditions are harsh, and the raw material triphenylphosphine used in it is expensive, resulting in high cost
Most of the by-products generated by the reaction are phosphorus-containing compounds, which are more polluting to the environment, and the content and yield of the final target product 2-(4-fluorophenyl)-3-(2-chlorophenyl)-propylene are also partial Low (up to only 13%), it is difficult to realize industrial production

Method used

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  • Method for preparing epoxiconazole intermediate
  • Method for preparing epoxiconazole intermediate
  • Method for preparing epoxiconazole intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0025] This embodiment provides a preparation method of 2-(4-fluorophenyl)-3-(2-chlorophenyl)-propene, which comprises the following steps:

[0026] (1), the synthesis of epoxy ester intermediate

[0027] Add 32g of ethanol in the reaction flask, dissolve 8.16g of sodium ethylate (0.12mol) in ethanol, add dropwise 12.4g of p-fluorobenzaldehyde (0.1mol) and 12.3g of ethyl chloroacetate (0.1004mol) in the system For the mixture, keep the temperature of the system at 10°C to 15°C during the dropwise addition process. After the dropwise addition, raise the temperature to 30°C and keep it warm for 3.5 hours. After the reaction is complete, remove ethanol, add water, and separate to obtain 20.5g of epoxy ester intermediate with a content of 94.3%. The rate is 92%.

[0028] (2), the synthesis of p-fluorophenylacetaldehyde

[0029] Add the 20.5g epoxy ester intermediate (content 94.3%, 0.092mol) that step (1) obtains in reaction bottle, be warming up to 40 ℃, add the sodium hydroxid...

Embodiment 2

[0035] This embodiment provides a preparation method of 2-(4-methoxyphenyl)-3-(2-chlorophenyl)-propene, which comprises the following steps:

[0036] (1), the synthesis of epoxy ester intermediate

[0037] Add 32g of ethanol and 6.48g of sodium methylate (0.12mol) in the reaction flask, add dropwise the mixture of 13.4g p-methoxybenzaldehyde (0.1mol) and 12.3g of ethyl chloroacetate (0.1004mol) at 10°C, dropwise After the temperature was raised to 30°C for 2 hours, ethanol was removed, and water was added to separate the mixture to obtain 21.7 g of an epoxy ester intermediate with a content of 90.3% and a yield of 89%.

[0038] (2), the synthesis of p-methoxyphenylacetaldehyde

[0039] Add the 21.7g epoxy ester intermediate (content 90.3%, 0.0894mol) that step (1) obtains in the reaction bottle, 35.6g 20% ​​sodium hydroxide aqueous solution (sodium hydroxide 0.178mol), react 2h at 40 ℃ , heated up to 90°C, added 152.4g of 20% dilute sulfuric acid (0.311mol of sulfuric acid),...

Embodiment 3

[0045] This embodiment provides a preparation method of 2-(4-fluorophenyl)-3-(4-chlorophenyl)-propene, which comprises the following steps:

[0046] (1), the synthesis of epoxy ester intermediate

[0047] Add 32g of methanol and 8.16g of sodium ethylate (0.12mol) in the reaction flask, add dropwise a mixture of 12.4g of p-fluorobenzaldehyde (0.1mol) and 12.3g of ethyl chloroacetate (0.1004mol) at 10°C, and the reaction ends Methanol was added to water layer to obtain 20.7 g of an epoxy ester intermediate with a content of 92.3% and a yield of 91.2%.

[0048] (2), the synthesis of p-fluorophenylacetaldehyde

[0049] Add the 20.7g epoxy ester intermediate (content 92.3%, 0.09mol) that step (1) obtains in reaction bottle, add the sodium hydroxide aqueous solution (sodium hydroxide 0.227mol) of 45.4g 20wt% at 40 ℃, end of reaction Raise the temperature to 90°C, add 154.4g of 20wt% dilute sulfuric acid (0.315mol of sulfuric acid), cool down to 30°C after 1h, and separate to obtai...

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Abstract

This invention discloses a method for preparing an epoxiconazole intermediate. The epoxiconazole intermediate is 2-(4-substituted phenyl)-3-(2-substituted phenyl)-propylene. The method comprises the following steps of: reacting para-substituted benzaldehyde with ethyl chloroacetate to generate the epoxiconazole intermediate in the presence of basic catalyst, then hydrolyzing and performing decarboxylation to the epoxyester intermediate with aqueous solution of sodium hydroxide and diluted sulfuric acid to generate para-substituted benzaldehyde; reacting the para-substituted benzaldehyde with ortho-substituted benzaldehyde to generate the epoxiconazole intermediate 2-(4-substituted phenyl)-3-(2-substituted phenyl)-acrolein, finally reducing the 2-(4-substituted phenyl)-3-(2-substituted phenyl)-acrolein by lithium aluminum hydride to generate the epoxiconazole intermediate. The process provided by the invention is simple in technology, and each reaction step can be finished under moderate conditions; the process is low in cost, and has little three wastes; in addition, the content and yield of the target product are higher and the process is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing an epoxiconazole intermediate, in particular to a method for preparing 2-(4-fluorophenyl)-3-(2-chlorophenyl)-propene. Background technique [0002] Epoxiconazole is a new type, broad-spectrum, long-lasting broad-spectrum fungicide, which has a good control effect on a series of cereal crop diseases such as leaf blight, powdery mildew, eye striae, etc. It can prevent and control sugar beet, peanut, coffee, rice and fruit trees and other diseases, and is a low-toxic and safe fungicide, which meets the World Health Organization's drug residue toxicity standard. In the past, the domestic market was mainly for export, but with the recognition of the domestic market, the share in the domestic fungicide market has grown steadily, and the product is cost-effective, and the market prospect is very promising. [0003] It is known that 2-(4-fluorophenyl)-3-(2-chlorophenyl)-propene is the most typical intermediate f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/24C07C17/35C07C43/225C07C41/18
Inventor 周彬鞠晓东蔡军义崔华李彩凤
Owner JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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