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Method for preparing 2-chlorine-4-fluorin-nitrobenzene sulfonyl chloride

A technology of nitrobenzenesulfonyl chloride and fluorobenzenesulfonyl chloride is applied in the field of preparation of organic synthesis intermediate 2-chloro-4-fluoro-5-nitrobenzenesulfonyl chloride, and can solve problems such as difficult preparation, difficult industrial production and the like , to achieve the effect of low cost, mild reaction conditions and good selectivity

Inactive Publication Date: 2005-08-31
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the starting material 4-chloro-2-fluoronitrobenzene of this method is relatively difficult to prepare (Chinese patent CN1162393C), and has not yet been commercially produced, making this method difficult to realize industrial production

Method used

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  • Method for preparing 2-chlorine-4-fluorin-nitrobenzene sulfonyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: Preparation of 2-chloro-4-fluorobenzenesulfonyl chloride

[0020] Add bis(2-chloro-4-fluorophenyl) disulfide (16.4g, 50mmol), 36% concentrated hydrochloric acid (76g, 750mmol) and 95% fuming nitric acid (10.9g, 150mmol) in a 250mL four-necked flask , stir and heat up to 70°C, slowly introduce chlorine gas, after 2.0h, the gas spectrum detects that the reaction is complete, cool to room temperature, stand and separate layers, the organic layer is washed with water, 10% sodium bicarbonate solution and water successively, and dried over anhydrous magnesium sulfate , and filtered to obtain 21.3 g of light yellow liquid, with a yield of 93.0% and a content of 98.5%.

Embodiment 2～6

[0021] Embodiment 2~6: Preparation of 2-chloro-4-fluorobenzenesulfonyl chloride

[0022] Reality

Embodiment 7

[0023] Example 7: Preparation of 2-chloro-4-fluoro-5-nitrobenzenesulfonyl chloride

[0024] Add 20% oleum (20.0 g, 50 mmol SO 3 ) and 95% fuming nitric acid (1.9g, 26mmol), 2-chloro-4-fluorobenzenesulfonyl chloride (4.6g, 20mmol) was added dropwise under stirring at room temperature, and the addition was completed in about 10min, and continued to stir at room temperature for 30min, and then heated to 80 Stir the reaction at ℃ for 3 h, the reaction is complete by gas spectrometry, cool to room temperature, let stand to separate the layers, extract the acid layer with chloroform (15mL×2), combine the organic layers, wash with water, 10% sodium bicarbonate solution and water successively, anhydrous Drying over magnesium sulfate and precipitation under reduced pressure gave 4.9 g of a light yellow solid with a yield of 89.4% and a content of 97.4%. The melting point is 60-62°C (literature value: 63-64°C).

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Abstract

A process for preparing 2-chloro-4-fluoro-5-nitrophenylsulfonyl chloride includes oxidizing reaction between bis (2-chloro-4-fluorophenyl) disulfide and chlorine gas under existance of concentrated sulfuric acid or smoke nitric acid, separating, purifying to obtain 2-chloro-4-fluorephenylsulfonyl chloride, and nitrifying reaction on smoke nitric acid under existance of concentrated sulfuric acid.

Description

(1) Technical field [0001] The invention relates to a preparation method of an important organic synthesis intermediate 2-chloro-4-fluoro-5-nitrobenzenesulfonyl chloride. (2) Background technology [0002] 2-Chloro-4-fluoro-5-nitrobenzenesulfonyl chloride is an important intermediate in organic synthesis, which can be used in the synthesis of pesticides such as the ultra-efficient herbicide fluthiacet-chloride. [0003] Japanese Patent Publication JP1-168622 treated 4-chloro-2-fluoronitrobenzene with chlorosulfonic acid to synthesize 2-chloro-4-fluoro-5-nitrobenzenesulfonyl chloride (Formula A). However, the starting material of this method, 4-chloro-2-fluoronitrobenzene, is difficult to prepare (Chinese patent CN1162393C), and has not yet been commercially produced, which makes it difficult to realize industrial production of this method. [0004] (3) Contents of the invention [0005] The purpose of the present invention is to provide a preparation method of 2-chloro...

Claims

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Application Information

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IPC IPC(8): C07C303/02C07C309/86
Inventor 杜晓华郑鹛徐振元
Owner ZHEJIANG UNIV OF TECH