Preparation process for 3-methyl-5-methoxybenzenesulfonyl chloride

A kind of technology of methoxybenzenesulfonyl chloride and methoxybenzenesulfonic acid, which is applied in the field of preparation of 3-methyl-5-methoxybenzenesulfonyl chloride, and can solve the problem that no literature reports 3-methyl-5-methylbenzene Oxybenzenesulfonyl chloride preparation technology and other problems, to achieve the effects of good application value, high yield, and easy post-processing

Inactive Publication Date: 2017-12-22
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But there is no preparation technology of bibliography 3-methyl-5-methoxybenzenesulfonyl chloride at present

Method used

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  • Preparation process for 3-methyl-5-methoxybenzenesulfonyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] A. Preparation of 3-methyl-5-bromophenylboronic acid

[0014] In a three-necked flask, 3,5-dibromotoluene (20.0g, 80.0mmol) was added to dry tetrahydrofuran (100mL), under N 2 Under protection, lower the temperature to -78°C, slowly add n-butyllithium (5.1g, 80.0mmol) dropwise, keep the temperature at -78°C and stir for 30min, add triisopropyl borate (22.6g, 120.0mmol), keep the reaction for 2h . After the reaction is complete, add water to quench, adjust the pH of the solution to 6 with 2mol / L dilute hydrochloric acid, extract with ethyl acetate (50mL×3), dry over anhydrous sodium sulfate, filter, distill the filtrate to remove the solvent under reduced pressure, and beat with n-hexane (30mL) , and dried to obtain 15.4 g of 3-methyl-5-bromophenylboronic acid as a white solid. The yield was 89.5%.

[0015] 1 H NMR (400MHz, CD 3 OD) δ7.65 (s, 1H), 7.48 (s, 1H), 7.37 (s, 1H), 2.32 (s, 3H).

[0016] B. Preparation of 3-methyl-5-bromophenol

[0017] In a three-necked...

Embodiment 2

[0028] A. Preparation of 3-methyl-5-bromophenylboronic acid

[0029] In a three-necked flask, add 3,5-dibromotoluene (20.0g, 80.0mmol) into dry dimethyltetrahydrofuran (100mL), and 2 Under protection, lower the temperature to -78°C, slowly add n-butyllithium (5.1g, 80.0mmol) dropwise, keep the temperature at -78°C and stir for 30min, add triisopropyl borate (22.6g, 120.0mmol), keep the reaction for 2h . After the reaction is complete, add water to quench, adjust the pH of the solution to 6 with 2mol / L dilute hydrochloric acid, extract with ethyl acetate (50mL×3), dry over anhydrous sodium sulfate, filter, distill the filtrate to remove the solvent under reduced pressure, and beat with n-hexane (30mL) , and dried to obtain 15.2 g of 3-methyl-5-bromophenylboronic acid as a white solid. The yield was 88.6%.

[0030] 1 H NMR (400MHz, CD 3 OD) δ7.65 (s, 1H), 7.48 (s, 1H), 7.37 (s, 1H), 2.32 (s, 3H).

[0031] B. Preparation of 3-methyl-5-bromophenol

[0032] In a three-necked...

Embodiment 3

[0043] A. Preparation of 3-methyl-5-bromophenylboronic acid

[0044] In a three-necked flask, 3,5-dibromotoluene (20.0g, 80.0mmol) was added to dry tetrahydrofuran (100mL), under N 2 Under protection, lower the temperature to -78°C, slowly add tert-butyllithium (5.1g, 80.0mmol) dropwise, keep the temperature at -78°C and stir for 30min, add triisopropyl borate (22.6g, 120.0mmol), keep the reaction for 2h . After the reaction is complete, add water to quench, adjust the pH of the solution to 6 with 2mol / L dilute hydrochloric acid, extract with ethyl acetate (50mL×3), dry over anhydrous sodium sulfate, filter, distill the filtrate to remove the solvent under reduced pressure, and beat with n-hexane (30mL) , and dried to obtain 15.5 g of 3-methyl-5-bromophenylboronic acid as a white solid. The yield was 90.3%.

[0045] 1 H NMR (400MHz, CD 3 OD) δ7.65 (s, 1H), 7.48 (s, 1H), 7.37 (s, 1H), 2.32 (s, 3H).

[0046] B. Preparation of 3-methyl-5-bromophenol

[0047] In a three-nec...

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Abstract

The invention discloses a preparation process for 3-methyl-5-methoxybenzenesulfonyl chloride. The process comprises the following steps: 3,5-dibromotoluene is used as an initial raw material, the 3,5-dibromotoluene is subjected to a boronic acidification reaction, thus 3-methyl-5-bromophenylboronic acid is obtained, the 3-methyl-5-bromophenylboronic acid is subjected to an oxidation reaction, thus 3-methyl-5-bromophenol is obtained, the 3-methyl-5-bromophenol is subjected to a substitution reaction, thus 3-methyl-5-bromoanisoles is obtained, the 3-methyl-5-bromoanisoles is subjected to sulfonation, thus 3-methyl-5-methoxybenzenesulfonate is obtained, the 3-methyl-5-methoxybenzenesulfonate is subjected to a substitution reaction, and therefore the objective compound 3-methyl-5-methoxybenzenesulfonyl chloride is obtained. According to the above route, the raw materials are easy to obtain, post-treatment is simple, convenient and easy to implement, a yield is relatively high, and the process has relatively-good application value.

Description

technical field [0001] The invention relates to a preparation process of 3-methyl-5-methoxybenzenesulfonyl chloride. It belongs to the field of organic synthesis, fine chemical industry and pharmaceutical intermediates. Background technique [0002] Methoxy-containing benzenesulfonyl chloride is an important intermediate in the field of medicine and dyes, which can be used to synthesize compounds such as thiol, sulfonamide, and arylsulfonate, and can also be used as an ultraviolet labeling reagent and Preparation of foaming agent for sulfonyl hydrazide polymer materials. In the field of medicine, methoxy-containing benzenesulfonyl chloride is a synthetic CRTH2 and CCR5 receptor antagonist, HIV-1 integrase inhibitor, and the treatment of HIV infection, asthma, rheumatoid arthritis, autoimmune diseases and chronic obstruction Important intermediates of drugs for diseases such as chronic pulmonary disease (COPD). But there is no literature report on the preparation technolog...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/02C07C309/87
Inventor 赵春深吴明圆黄筑艳
Owner GUIZHOU UNIV
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