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Preparation method of 5-halo-2-alkyloxy-4-toluene sulfochloride

A technology of toluenesulfonyl chloride and alkoxy, which is applied in the field of synthesis of chemical raw material intermediates, can solve the problems of difficult raw materials, unsuitable for industrial production, and high synthesis cost, and achieve the effects of short reaction time, low raw material cost, and relatively low raw material cost

Inactive Publication Date: 2017-05-17
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials used in this synthesis process are difficult to purchase, the synthesis cost is high, the operation process needs to be performed under low temperature environment, and the highly toxic chlorosulfonic acid is used as a reagent, which is not suitable for industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] A. Preparation of 1-chloro-4-methoxy-2-methylbenzene

[0021] In a 500mL single-necked bottle, dissolve 4-chloro-3-methylphenol (20.0g, 140.3mmol), potassium carbonate (58.2g, 420.8mmol) in N,N-dimethylformamide (150mL), drop slowly Add iodomethane (23.9g, 168.3mmol), dropwise, react at room temperature for 2h. After the reaction was completed, the reaction solution was poured into ice water, extracted with methyl tert-butyl ether (60mL×3), the organic phases were combined, dried with anhydrous sodium sulfate, and the solvent N,N-dimethylformamide was distilled off under reduced pressure. , 18.1 g of 1-chloro-4-methoxy-2-methylbenzene was obtained, and the yield was 82.3%;

[0022] B. Preparation of 5-chloro-2-methoxy-4-toluenesulfonyl chloride

[0023] In a 250mL three-necked flask, add 1-chloro-4-methoxy-2-methylbenzene (18.1g, 115.4mmol), and slowly add sulfonyl chloride (16.1g, 138.4mmol) dropwise under ice bath conditions, and react at room temperature 1h. Afte...

Embodiment 2

[0026] A. Preparation of 1-chloro-4-methoxy-2-methylbenzene

[0027] In a 500mL single-necked bottle, 4-chloro-3-methylphenol (20.0g, 140.3mmol), sodium bicarbonate (47.1g, 561.1mmol) were dissolved in tetrahydrofuran (150mL), and iodomethane (23.89g, 168.3mmol), after dropping, react at room temperature for 2h. After the reaction was completed, the reaction solution was poured into ice water, extracted with methyl tert-butyl ether (60mL×3), the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent tetrahydrofuran was distilled off under reduced pressure to obtain 1-chloro-4- Methoxy-2-methylbenzene 18.0 g, yield 81.9%.

[0028] B. Preparation of 5-chloro-2-methoxy-4-toluenesulfonyl chloride

[0029] In a 250mL three-necked flask, add 1-chloro-4-methoxy-2-methylbenzene (18.0g, 114.8mmol), and slowly add sulfuryl chloride (16.1g, 137.8mmol) dropwise under ice-bath conditions, and react at room temperature 1h. After the reaction was completed, th...

Embodiment 3

[0032] A. Preparation of 1-chloro-4-methoxy-2-methylbenzene

[0033] In a 500mL single-necked bottle, 4-chloro-3-methylphenol (20.0g, 140.3mmol), triethylamine (71.0g, 701.4mmol) were dissolved in acetone (150mL), slowly added dropwise methyl iodide (39.8g, 280.5mmol), after dropping, react at room temperature for 1h. After the reaction was completed, the reaction solution was poured into ice water, extracted with methyl tert-butyl ether (60mL×3), the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent acetone was distilled off under reduced pressure to obtain 1-chloro-4- Methoxy-2-methylbenzene 18.3g, yield 83.2%.

[0034] B. Preparation of 5-chloro-2-methoxy-4-toluenesulfonyl chloride

[0035] In a 250mL three-necked flask, add 1-chloro-4-methoxy-2-methylbenzene (18.3g, 116.6mmol), and slowly add sulfuryl chloride (17.7g, 151.6mmol) dropwise under ice-bath conditions, and react at room temperature 1h. After the reaction was completed, the r...

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Abstract

The invention relates to the technical field of chemical material intermediate synthesis, in particular to a preparation method of 5-halo-2-alkyloxy-4-toluene sulfochloride. The 5-halo-2-alkyloxy-4-toluene sulfochloride is formed by taking cheap and available 4-halo-3-methylphenol as a raw material and performing etherification reaction and sulfonylation reaction, the yield can reach 64 percent, the material cost is relatively low, the technical operation is simple, the reaction condition is mild, the reaction time is short, and industrialization is easy to realize.

Description

technical field [0001] The invention relates to the technical field of synthesis of chemical raw material intermediates, in particular to a preparation method of 5-halo-2-alkoxy-4-toluenesulfonyl chloride. Background technique [0002] Benzenesulfonyl chloride can be used to prepare sulfonamides, sulfonated esters and sulfones, and is an important intermediate for pesticides, dyes, and medicines. 5-Halo-2-methoxy-4-methylbenzenesulfonyl chloride is a derivative of benzenesulfonyl chloride. In the prior art, there are a large number of 5-halo-2-methoxy-4-methyl The application of benzenesulfonyl chloride, such as the introduction of literature number KR2014144548 for 5-HT6 receptor antagonists, WO2009015897 for mGlu5 receptor antagonists, WO2009127417 for AXL kinase inhibitors, etc. [0003] At present, for the preparation of 5-halo-2-methoxyl-4-methylbenzenesulfonyl chloride, there are only a small amount of research reports through searching, mainly those reported by Al-Hi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/87C07C303/10
CPCC07C303/10C07C41/16
Inventor 刘力权文张梦辉黄筑艳
Owner GUIZHOU UNIV