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Synthetic method of o-chlorobenzylmagnesium chloride

A technology of o-chlorobenzylmagnesium chloride and its synthesis method, which is applied in the direction of magnesium organic compounds, etc., and can solve the problems of poor control of reaction temperature, difficulty in realizing industrial application, and low boiling point of solvents.

Inactive Publication Date: 2017-01-04
HAIZHENG CHEM NANTONG CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Wherein the compound o-chlorobenzylmagnesium chloride is the key intermediate for the synthesis of prothioconazole. For its synthetic method literature, the disposable drop method is mostly used, and the solvents used are ether, methyl tert-butyl ether, tetrahydrofuran, etc., these methods There are low boiling point of the solvent used, poor control of reaction temperature, many side reactions, and difficulty in industrial application.

Method used

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  • Synthetic method of o-chlorobenzylmagnesium chloride

Examples

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Effect test

Embodiment 1

[0022] Example 1: In a 2000 mL four-neck flask, add 45.3 g of newly produced magnesium chips, 0.1 g of iodine and 100 g of cyclopentyl methyl ether, and replace with nitrogen three times while stirring. While stirring, under the protection of nitrogen, add 10 g o-chlorobenzyl chloride at one time, the reaction is initiated within about 5-15 minutes, and the temperature begins to rise to 40°C. Add 500 g of cyclopentyl methyl ether within 10 minutes, and when the temperature reaches 25°C, turn on the ice-water bath, and start to drop a solution of o-chlorobenzyl chloride (190 g of o-chlorobenzyl chloride dissolved in 500 g of cyclopentyl methyl ether) base ether), and control the temperature between 20-30°C. After about 3 hours of dripping, after 30 minutes of dripping, the sample was quenched and detected by GC. The yield of the obtained o-chlorobenzyl magnesium chloride was 97%, and the purity was 95%.

Embodiment 2

[0023] Example 2: In a 2000 mL four-neck flask, add 45.3 g of newly produced magnesium chips, 0.1 g of iodine and 100 g of cyclopentyl methyl ether, and replace with nitrogen three times while stirring. While stirring, under the protection of nitrogen, add 10 g o-chlorobenzyl chloride at one time, the reaction is initiated within about 5-15 minutes, and the temperature begins to rise to 40°C. Add 500 g of xylene within 10 minutes, and when the temperature reaches 25°C, turn on the ice-water bath, and start to add a solution of o-chlorobenzyl chloride (190 g of o-chlorobenzyl chloride dissolved in 500 g of toluene), and control the temperature at 20- between 30°C. After about 3 hours of dripping, after 30 minutes of dripping, the sample was quenched and detected by GC. The yield of the obtained o-chlorobenzyl magnesium chloride was 94%, and the purity was 92%.

Embodiment 3

[0024] Example 3: In a 2000 mL four-neck flask, add 45.3 g of newly produced magnesium chips, 0.1 g of iodine and 100 g of 2-methyltetrahydrofuran, and replace with nitrogen three times while stirring. While stirring, under the protection of nitrogen, add 10 g o-chlorobenzyl chloride at one time, the reaction is initiated within about 5-15 minutes, and the temperature begins to rise to 40°C. Add 500 g of 2-methyltetrahydrofuran within 10 minutes. When the temperature reaches 25°C, turn on the ice-water bath and start to add a solution of o-chlorobenzyl chloride (190 g of o-chlorobenzyl chloride dissolved in 500 g of 2-methyltetrahydrofuran ), control the temperature between 20-30°C. After about 3 hours of dripping, after 30 minutes of dripping, the sample was quenched and detected by GC. The yield of the obtained o-chlorobenzyl magnesium chloride was 92%, and the purity was 91%.

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Abstract

The invention relates to a synthetic method of o-chlorobenzylmagnesium chloride. A reaction is carried out by using a specific solvent at the molar ratio of o-chlorobenzyl chloride to magnesium chips being 1: 1.1-1:3.0, preferably 1:1.5. Especially, a reaction trigger step exists in specific process. Especially after reaction triggering, temperature rises to 35-80 DEG C, preferably 35-45 DEG C. By the synthetic method, the purposes of easy industrialization, reaction safety, high yield, less side reaction and green synthesis can be achieved.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a synthesis method of o-chlorobenzylmagnesium chloride. [0002] technical background [0003] Prothioconazole is a new broad-spectrum triazolethione fungicide developed by Bayer, patent number: WO9616048, application date: November 8, 1995, and its mechanism of action is to inhibit the precursor of sterol in fungi - lanosterol or The demethylation at the 14-position of 24-methylene dihydrolanosterol not only has good systemic activity, excellent protection, treatment and eradication activities, but also has a long duration. Since 2004, it has been registered in many countries, occupying the third place in Bayer's top 10 product list, and its sales in 2013 reached 750 million US dollars. The European PCT and Chinese patents of prothioconazole expired on November 7, 2015, and the following day, its US patent expired. Wherein the compound o-chlorobenzylmagnesium chloride is the k...

Claims

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Application Information

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IPC IPC(8): C07F3/02
CPCC07F3/02
Inventor 王建忠包如胜罗洪波王丽敏蒋富国徐坚勇
Owner HAIZHENG CHEM NANTONG CO LTD
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