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2(2-chlorine-4-phenyl fluoride) bisulfide, preparation and aplication

A technology of disulfide and fluorophenyl, which is applied to the preparation method and application field of new substances, can solve problems such as difficult preparation and difficult industrial production, and achieve the effects of simple operation, mild reaction conditions and reasonable route.

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

[0005] 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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  • 2(2-chlorine-4-phenyl fluoride) bisulfide, preparation and aplication
  • 2(2-chlorine-4-phenyl fluoride) bisulfide, preparation and aplication
  • 2(2-chlorine-4-phenyl fluoride) bisulfide, preparation and aplication

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: Preparation of bis(4-amino-2-chlorophenyl) disulfide

[0022] Add 3,4-dichloronitrobenzene (96.0g, 0.5mol) and water (150mL) into a 1000mL four-necked flask, raise the temperature to 50~55℃, add sodium sulfide nonahydrate (360.0g, 1.5 mol), sulfur (24.0g, 0.75mol) and water (210mL), add it in 10min, then heat to reflux for 10-12h, HPLC analysis has completed the reaction; azeotropic distillation separated a small amount of by-products 3,4- Dichloroaniline (2.5g, yield 3.1%), at this time about 150mL of water is distilled out; add 150mL of water to the reaction solution and adjust the temperature to 45℃, cool in a water bath, add 30% hydrogen peroxide dropwise at 40~50℃ (56.7g, 0.5mol), cool to room temperature after adding, filter with suction, wash with water, and recrystallize with ethanol to obtain 76.5g of orange-yellow crystals, yield 95.0%, content 98.3%, melting point 190.5-192.0°C.

Embodiment 2～5

[0023] Examples 2~5: Preparation of bis(4-amino-2-chlorophenyl) disulfide

[0024]

Embodiment 6

[0025] Example 6: Preparation of bis(2-chloro-4-fluorophenyl) disulfide

[0026] In a 500ml three-necked flask, add bis(2-chloro-4-aminophenyl) disulfide (20.0g, 62mmol) and 30% dilute sulfuric acid (250g), stir at room temperature for 1 hour, and cool to 5-10°C in an ice-water bath. Then, 30% sodium nitrite aqueous solution (29.7g, 129mmol) was added dropwise within 30min at this temperature, and after the addition, the reaction was continued with stirring at 5-10°C for 1.5h. A small amount of insoluble matter was removed by suction filtration. The filtrate was slowly added with 40% fluoroboric acid aqueous solution (33g, 150mmol) under cooling in an ice-water bath, and the reaction temperature was controlled at 5~10℃ and stirred for 30min. 1:10) The solution was washed with ether and dried in vacuum to obtain a pale yellow powdery diazonium fluoroborate (30.5g); the obtained diazonium salt was placed in a dry 250mL three-necked flask, and the temperature was carefully raised to ...

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Abstract

A novel bis (2-chloro-4-fluorophenyl) bisulfide is prepared from 3,4-dichloronitrobenzene, sodium sulfide, sulfur, H2O2, sodium nitrite, fluoroboric acid, hydrochloric acid, nitric acid and smoke sulfuric acid. Its application is also disclosed. Its advantages are high purity and selectivity.

Description

(1) Technical field [0001] The invention relates to a new substance bis(2-chloro-4-fluorophenyl) disulfide, and a preparation method and application of the new substance. (2) Background technology [0002] 2-Chloro-4-fluoro-5-nitrobenzenesulfonyl chloride is an important organic synthesis intermediate, which can be used in the synthesis of super-efficient herbicide fluthiacet-ethyl and other pesticides. [0003] Japanese Patent Publication JP1-168622 treated 4-chloro-2-fluoronitrobenzene with chlorosulfonic acid to synthesize 2-chloro-4-fluoro-5-nitrobenzenesulfonyl chloride (see formula A). [0004] [0005] However, 4-chloro-2-fluoronitrobenzene, the starting material of this method, is difficult to prepare (Chinese Patent CN1162393C), and it has not yet been commercialized, making it difficult for this method to achieve industrial production. (3) Summary of the invention [0006] The present invention is to provide a new substance that can be used to prepare 2-chloro-4-fluo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/22C07C323/09
Inventor 杜晓华徐振元
Owner ZHEJIANG UNIV OF TECH
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