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Preparation method of 6-substituted-2-trifluoromethylbenzenesulfonyl chloride

A technology of trifluoromethylbenzenesulfonyl chloride and chlorine substitution, which is applied in the preparation of sulfonic acid and organic chemistry, can solve the problems of complex reaction control conditions, low product yield, and difficult separation, and achieve simple process control conditions and high product quality. The effect of high yield and easy price

Active Publication Date: 2015-06-10
NANJING LYNSCI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] This method also needs to be reacted at extremely low temperature, and a large amount of heavily polluted sulfur dioxide and strong irritating compound sulfuryl chloride are used. The reaction control conditions are complex, separation is difficult, and the product yield is low.

Method used

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  • Preparation method of 6-substituted-2-trifluoromethylbenzenesulfonyl chloride
  • Preparation method of 6-substituted-2-trifluoromethylbenzenesulfonyl chloride
  • Preparation method of 6-substituted-2-trifluoromethylbenzenesulfonyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1: the preparation of 2,3-difluorobenzotrifluoride

[0051]

[0052] Put 215g (1.00mol) of the compound of formula (II) 2,3-dichlorobenzotrifluoride, 140g (2.41mol) of anhydrous potassium fluoride, 2000mL of sulfolane, and 10g of tetraphenylphosphine bromide into the autoclave in batches, Under stirring, heat up to 250-300° C. and keep warm for 20 hours. Cool and filter to remove the generated potassium chloride and excess potassium fluoride. The filtrate was rectified, and the fraction from 112°C to 119°C was collected to obtain the compound 2,3-difluorobenzotrifluoride of formula (III); the residue continued to be rectified to collect the fraction at 145°C-151°C to obtain the by-product 2-fluoro-3 -Chlorotrifluorotoluene; the by-product can be recycled and applied. After applying mechanically, the average yield of continuous preparation formula (III) compound 2,3-difluorobenzotrifluoride is: 87.6%, HNMR (CH 3 OD, 300 MHz): δ 7.35-7-422 (m, 2H), 7.17-7...

Embodiment 2

[0053] Embodiment 2: Preparation of 6-fluoro-2-trifluoromethyl phenethyl sulfide

[0054]

[0055] Add 182g (1.00mol) of compound 2,3-difluorobenzotrifluoride of formula (III), 500mL of solvent N,N-dimethylformamide, and 200g (1.45mol) of acid-binding agent potassium carbonate into the reaction flask respectively, and place on ice Under bath cooling, control -5°C-5°C, add 65 g (1.05 mol) of ethanethiol dropwise, and drop it in about 3 hours. After the drop, the temperature was raised to 50°C to continue the reaction for 3 hours. The reaction was followed by GC, and the reaction was terminated when the content of the raw material 2,3-difluorobenzotrifluoride was less than 3%. Remove the generated potassium fluoride and excess potassium carbonate by filtration, rectify the filtrate under reduced pressure, and collect the fraction at 115-125°C (50-80mmHg) to obtain the compound 6-fluoro-2-trifluoromethylbenzene of formula (IV) Thioether 175g, yield: 78.13%, content: 96.3%; H...

Embodiment 3～10

[0056] Embodiment 3~10: the preparation of formula (IV) compound 6-fluoro-2-trifluoromethyl phenyl alkyl sulfide

[0057]

[0058] Synthetic method is with embodiment 2, and the ethanethiol in embodiment 2 is changed into corresponding R in table 1 1 The hydrocarbon thiol (M is hydrogen) or its alkali metal salt (M is a metal ion) is reacted in a corresponding solvent, and the experimental data are shown in Table 1.

[0059] Synthetic method and data of table 1 formula (IV) compound

[0060]

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Abstract

The invention relates to a preparation method of 6-substituted-2-trifluoromethylbenzenesulfonyl chloride as a key intermediate of sulfonamide or sulfonylurea herbicides. The method comprises the following steps: 6-fluoro-2-trifluoromethylbenzenethioether is formed through fluorine displacement and sulfenyl group substitution of a raw material 2,3-dichlorobenzotrifluoride, chlorine oxidative chloridization or substitution of 6-fluoro-2-trifluoromethylbenzenethioether is carried out, and then chlorine oxidative chloridization of the finally obtained material is carried out to obtain the above product. The method has the advantages of easily available raw materials, simple process, high yield and low cost.

Description

technical field [0001] The invention relates to a preparation method of the key intermediate 6-substituted-2-trifluoromethylbenzenesulfonyl chloride of sulfonamide or sulfonylurea herbicides. Background technique [0002] Sulfonamide or sulfonylurea herbicides are broad-spectrum and high-efficiency herbicides targeting acetolactate synthase. The parent structure of this type of herbicide is a substituted benzenesulfonamide or benzenesulfonylurea. Penoxsulam developed by Dow AgroSciences belongs to this kind of agricultural herbicide. This product was officially registered in the US EPA on September 24, 2004, and was promoted in the southern rice areas of the United States in 2005. Application, registered in China in 2008, the dosage form currently registered in my country is 2.5% oil suspension concentrate. Penoxsulam is a conductive broad-spectrum herbicide for paddy fields. It is absorbed by stems, leaves, young shoots and roots, and then transmitted to meristems through x...

Claims

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Application Information

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IPC IPC(8): C07C309/86C07C303/02
Inventor 陈正伟肖涛朱家豪于传宗戴建新
Owner NANJING LYNSCI CHEM
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