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Preparation method of 2-fluoro-6-trifluoromethylbenzenesulfonylchloride

A technology of trifluoromethylbenzenesulfonyl chloride and trifluorotoluene, which is applied in the field of organic synthesis and can solve problems such as odor, high process risk, and high risk

Inactive Publication Date: 2018-04-20
HANDAN ZHAODU FINE CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the patent (US5858924) applied by Dow AgroSciences in 1999, a preparation method using 2-fluoro-6-trifluoromethylaniline as a raw material was reported. The raw material of this method is expensive and not easy to obtain; Fluorotoluene is a raw material, and n-butyllithium is used as a base, reacted with dialkyl sulfide, and 2-fluoro-6-trifluoromethylbenzenesulfonyl chloride is prepared by the method of chlorine oxidation, and the by-product mercaptan of this method is organic Smelly substances, the production environment has a strong smell, and chlorine gas is used as an oxidant, which is highly toxic and dangerous; in addition, using n-butyllithium as a base, m-fluorobenzotrifluoride, sulfur dioxide and chlorine can also react to prepare 2-fluoro-6 -Trifluoromethylbenzenesulfonyl chloride, but also use highly toxic sulfur dioxide and chlorine, the process risk is greater

Method used

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  • Preparation method of 2-fluoro-6-trifluoromethylbenzenesulfonylchloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Add 150 mL of tetrahydrofuran and 16.4 g (0.1 mol) of m-fluorobenzotrifluoride into a 500 mL three-necked flask, cool down to -70°C, and slowly add 52 mL of 2M n-butyllithium n-hexane solution dropwise under nitrogen protection. Control the rate of addition so that the temperature of the reaction solution is not higher than -50°C. After dropping, the reaction system was evacuated to -0.09Mpa, and sulfuryl fluoride gas was introduced, and white precipitates gradually appeared in the reaction system. The sulfuryl fluoride gas was fed continuously until 11 g of gas was fed and stopped. Keep the temperature of the reaction system at -40~-20°C for 4 hours, add 2 mL of water to quench the reaction, and stir for 15 minutes. The white solid of lithium fluoride generated by separation was filtered off, and the filtrate was distilled off under normal pressure to remove n-hexane and tetrahydrofuran. Add 100mL dichloromethane to the distilled raffinate, add 15g calcium chloride i...

Embodiment 2

[0021] Add 400mL tetrahydrofuran and 49.2g (0.3mol) m-fluorobenzotrifluoride to a 1000mL stainless steel kettle, cool down to -60°C, and slowly add 160mL of 2M n-butyllithium n-hexane solution dropwise under nitrogen protection. Control the rate of addition so that the temperature of the reaction solution is not higher than -30°C. After dripping, the reaction system was evacuated to -0.095Mpa, 46g of sulfuryl fluoride gas was introduced, and the temperature of the reaction system was kept at -30°C for 6 hours, and 4mL of water was added to quench the reaction, and stirred for 15 minutes. The white solid of lithium fluoride generated by separation was filtered off, and the filtrate was distilled to remove n-hexane and dioxane. Add 300mL chloroform to the distilled raffinate, add 50g calcium chloride in 300mL water solution, stir at 60°C for reaction, white precipitate gradually precipitates in the mixture, stop the reaction for 2 hours, filter and separate the liquid, and use 1...

Embodiment 3

[0023] 150 mL of dioxane and 16.4 g (0.1 mol) of m-fluorobenzotrifluoride were added to a 500 mL stainless steel kettle, the temperature was lowered to -80°C, and 55 mL of 2M n-butyllithium n-hexane solution was slowly added dropwise under nitrogen protection. Control the rate of addition so that the temperature of the reaction solution is not higher than -50°C. After dropping, the reaction system was evacuated to -0.095Mpa, and 15g of sulfuryl fluoride gas was introduced, and the system was naturally heated to 0°C, and the temperature of the reaction system was kept at 0-10°C for 3 hours, and 0.5mL of water was added to quench the reaction, and stirred 15 minutes. The white solid of lithium fluoride generated by separation was filtered off, and the filtrate was distilled to remove n-hexane and dioxane. Add 100mL of dichloromethane to the distilled raffinate, add 18g of calcium chloride in 100mL of water, stir at room temperature, a white precipitate gradually precipitates in...

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Abstract

The invention provides a preparation method of 2-fluoro-6-trifluoromethylbenzenesulfonylchloride. The method comprises the following steps: reacting fluoro-3-benzene and alkali serving as main raw materials in an organic solvent to generate a corresponding salt; reacting the generated salt with sulfuryl fluoride under a certain pressure to generate 2-fluoro-6-trifluoromethanesulphonyl fluoride; reacting filtered and distilled reaction liquid with calcium chloride in a mixed solution; filtering, separating and desolventizing the reaction liquid to obtain liquid-state 2-fluoro-6-trifluoromethylbenzenesulfonylchloride of which the yield is 85 percent or more and the purity is 96 percent or more. The preparation method of the 2-fluoro-6-trifluoromethylbenzenesulfonylchloride provided by the invention has the advantages of no use of highly-toxic or poisonous gas, mild conditions, easiness in controlling, adoption of readily-available raw materials, lower cost, no three waste (waste water, waste solid and waste gas) discharge, and suitability for industrial production.

Description

technical field [0001] The invention relates to 2-fluoro-6-trifluoromethylbenzenesulfonyl chloride, especially a preparation method of 2-fluoro-6-trifluoromethylbenzenesulfonyl chloride, which belongs to the field of organic synthesis. Background technique [0002] Penoxsulam is a triazolopyrimidine sulfonamide herbicide developed by Dow AgroSciences, which can effectively kill barnyardgrass and annual Cyperaceae weeds, and is effective against a variety of broad-leaved weeds. One of the most widely used herbicides. [0003] 2-fluoro-6-trifluoromethylbenzenesulfonyl chloride is one of the key intermediates for the preparation of penoxsulam. In the patent (US5858924) applied by Dow AgroSciences in 1999, a preparation method using 2-fluoro-6-trifluoromethylaniline as a raw material was reported. The raw material of this method is expensive and not easy to obtain; Fluorotoluene is a raw material, and n-butyllithium is used as a base, reacted with dialkyl sulfide, and 2-fluoro...

Claims

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Application Information

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IPC IPC(8): C07C303/02C07C309/86
CPCC07C303/02C07C303/04C07F1/02C07C309/86
Inventor 赵永平王运红时建刚丁金囤司小东
Owner HANDAN ZHAODU FINE CHEM CO LTD
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