Preparation method of epoxiconazole intermediate (Z)-2-(4-fluorophenyl)-1-(2-chlorphenyl)-3-halogen propylene

A technology of halogenated propylene and chlorophenyl, which is applied in the preparation of halogenated hydrocarbons, chemical instruments and methods, organic chemistry, etc., can solve the problems of high cost and low yield, achieve less side reactions, high product yield, Simple operation effect

Active Publication Date: 2014-07-23
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
View PDF4 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But adopt this method to prepare the alkene, the E formula isomer occupies a large part ratio, causes productive rate to be lower, and the reaction cost of p-fluoroacetophenone and 2-chlorobenzylidenetriphenylphosphine chloride is relatively low. high

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of epoxiconazole intermediate (Z)-2-(4-fluorophenyl)-1-(2-chlorphenyl)-3-halogen propylene
  • Preparation method of epoxiconazole intermediate (Z)-2-(4-fluorophenyl)-1-(2-chlorphenyl)-3-halogen propylene
  • Preparation method of epoxiconazole intermediate (Z)-2-(4-fluorophenyl)-1-(2-chlorphenyl)-3-halogen propylene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0016] The technical solutions of the present invention will be further described below in conjunction with specific examples, but the present invention is not limited to these examples. In these examples, unless otherwise stated, all reagents used were of reagent grade and measured in grams (g).

[0017] (1) Synthesis of o-chlorophenylacetyl chloride - thionyl chloride method

[0018] Add 17.0g (0.1mol) of o-chlorophenylacetic acid into the reaction flask, add 500mL of dichloromethane and stir to dissolve, then add 0.2g of DMF as a catalyst, raise the temperature to 35°C, add 17.8g (0.15mol) of thionyl chloride dropwise To the above solution, the dropwise addition was completed in one hour, then the temperature was raised to 45° C., and the reaction was terminated after reflux reaction for 3 hours. The solvent and excess thionyl chloride were distilled off to obtain 18.5 g (0.098 mol) of o-chlorophenylacetyl chloride, with a yield of 98%.

[0019] (2) Synthesis of o-chlorop...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to the field of pesticides, and particularly relates to a preparation method of an epoxiconazole intermediate (Z)-2-(4-fluorophenyl)-1-(2-chlorphenyl)-3-halogen propylene. The method includes: reacting o-clorophenylacetic acid and a chlorinating agent under the catalysis of dimethyl formamide to obtain o-chlorophenylacetyl chloride; subjecting the o-chlorophenylacetyl chloride and fluorobenzene to acylation under the catalysis of aluminium chloride to obtain 2-chlorophenyl-4'-fluoroacetophenone; subjecting the 2-chlorophenyl-4'-fluoroacetophenone and methyltriphenylphosphonium bromide under alkaline conditions to a Wittig reaction to obtain an olefin; and reacting the olefin with a halogenating agent to obtain the (Z)-2-(4-fluorophenyl)-1-(2-chlorphenyl)-3-halogen propylene. The method has characteristics of simple process, mild reaction conditions, high selectivity of the needed isomer after halogenation (namely high ratio of the Z isomer), and high content and yield of the target product.

Description

technical field [0001] The invention relates to the field of pesticides, in particular to a preparation method of epoxiconazole intermediate (Z)-2-(4-fluorophenyl)-1-(2-chlorophenyl)-3-halopropene. Background technique [0002] Epoxiconazole is a new, broad-spectrum, long-lasting fungicide developed by BASF in 1985. It is a new type of important triazole fluorine-containing fungicide. At present, there are two main synthetic routes in industrial production: epoxidize compound I, and then react with 1,2,4-triazole to obtain epoxiconazole, that is, epoxidize first; or compound I and 1, 2,4-Triazole is reacted to prepare compound II, and then epoxidized to obtain epoxiconazole, that is, post-epoxidation. At present, patents that adopt epoxidation first include EP196038 and WO2007000759; patents that adopt post-epoxidation include US5245042 and CN101513183. In the above patents, regardless of whether the epoxidation is performed first or after the epoxidation, the target compo...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/24C07C17/14
Inventor 姜鹏孟至
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap