Epoxiconazole intermediate 1-chloro-3-(2-chlorophenyl)-2-(4-fluorophenyl)-2-propanol synthesis process

A synthesis process and a technology for intermediates, applied in the field of fine chemicals, can solve the problems of difficult industrial production, seldom application of aryl ketone compounds, poor safety, etc., and achieve low equipment consumption and energy consumption, easy solvent recovery, and easy operation. safe effect

Active Publication Date: 2015-12-09
内蒙古佳瑞米精细化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] But the synthesis of 1-chloro-3-(2-chlorobenzene)-2-(4-fluorobenzene)-2-propanol requires Grignard reaction, while documents US5081317 and US5268517 report that a large amount of ether is used as a solvent for the synthesis of this compound , production safety is poor, it is difficult to realize industrial production
Documents EP415247, WO9302086, and US5099040 respectively report the Grignard reaction involving methyl tert-butyl, diethoxymethane, toluene / tetrahydrofuran as a solvent of o-chlorobenzyl chloride, but they are all applied to the reaction with alkyl-substituted ketones. The reaction of aryl ketones is rarely used

Method used

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  • Epoxiconazole intermediate 1-chloro-3-(2-chlorophenyl)-2-(4-fluorophenyl)-2-propanol synthesis process
  • Epoxiconazole intermediate 1-chloro-3-(2-chlorophenyl)-2-(4-fluorophenyl)-2-propanol synthesis process
  • Epoxiconazole intermediate 1-chloro-3-(2-chlorophenyl)-2-(4-fluorophenyl)-2-propanol synthesis process

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Embodiment 1

[0027] This embodiment is the synthesis of 1-chloro-3-(2-chlorobenzene)-2-(4-fluorobenzene)-2-propanol, and the specific process is as follows:

[0028] Put 17.5g of magnesium chips (0.729mol, 99%, 1.2eq.) into the 1000mL four-necked bottle replaced by nitrogen, put 40g of diethoxymethane into it, and protect the whole process with nitrogen at a temperature of 20-25°C; 10g (0.06mol, 99%, 0.1eq.) of o-chlorobenzyl chloride was added dropwise in the middle, and the dropwise addition was completed in 5 minutes, and the temperature was naturally raised, and the reaction was initiated; Add dropwise the remaining 87.5g of o-chlorobenzyl chloride (0.54mol, 99%, 0.9eq.); after the dropwise addition (about 1h), keep the temperature at 10-15°C for 1h to obtain the Grignard reagent, and take a sample for analysis.

[0029] After the Grignard reagent was prepared, the Grignard reagent was transferred into a 2000mL four-neck flask under nitrogen protection; the Grignard reagent was cooled ...

Embodiment 2

[0032] This example is the synthesis of 1-chloro-3-(2-chlorobenzene)-2-(4-fluorobenzene)-2-propanol, the difference from Example 1 is that the reaction solvent is toluene and diethoxy The mixed solvent of methyl methane, the weight ratio of toluene, diethoxymethane and o-chlorobenzyl chloride is 2.6:1.3:1, and the molar ratio of magnesium and o-chlorobenzyl chloride is 1.2:1.

Embodiment 3

[0034] This example is the synthesis of 1-chloro-3-(2-chlorobenzene)-2-(4-fluorobenzene)-2-propanol, the difference from Example 1 is that the reaction solvent is toluene and diethoxy The mixed solvent of methyl methane, the weight ratio of toluene, diethoxymethane and o-chlorobenzyl chloride is 1.3:2.6:1, and the molar ratio of magnesium and o-chlorobenzyl chloride is 1.2:1.

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Abstract

The present invention discloses an epoxiconazole intermediate 1-chloro-3-(2-chlorophenyl)-2-(4-fluorophenyl)-2-propanol synthesis process, and belongs to the technical field of fine chemical industry. According to the process, 2-chlorobenzyl chloride and 2-chloro-4'-fluoroacetophenone are adopted as raw materials, diethoxymethane and toluene are adopted as solvents, and a two-step reaction comprising as a Grignard reaction and a nucleophilic addition reaction is performed to obtain the target product. According to the present invention, the high yield intermediate is obtained while the process operation is simplified, the raw material cost and the production cost are reduced, the environmental pollution is reduced, and the safety requirements of the industrial scale-up production are met.

Description

technical field [0001] The invention relates to the technical field of fine chemicals, in particular to a synthesis process of 1-chloro-3-(2-chlorobenzene)-2-(4-fluorobenzene)-2-propanol. Background technique [0002] Epoxiconazole, trade name Opus, chemical name (2RS, 3RS)-1-[3-(2-chlorophenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl ]-1 H -1,2,4-Triazole is a broad-spectrum triazole fungicide developed by BASF in Germany. It is mainly used for a series of cereal crop diseases such as blight, powdery mildew, eye sheath and more than ten kinds. It has a good control effect on diseases, and can control diseases in sugar beet, peanut, rapeseed, lawn, coffee, rice and fruit trees. Epoxiconazole is a kind of systemic triazole fungicide, its active ingredient epoxiconazole inhibits the synthesis of ergosterol of pathogenic bacteria, hinders the formation of bacterial cell wall, and epoxiconazole molecule has a certain effect on a fungal enzyme (14-dencthylase) Strong affinity, comp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/46C07C29/40
CPCC07C29/40C07F3/02C07C33/46
Inventor 李雨徐德胜吕超王鹤王荣良
Owner 内蒙古佳瑞米精细化工有限公司
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