2007•Unpublished venueRequires access

Synthesis of 3-Chloro-4-methyl-methylsulfonylbenzene as an Intermediate of Sulcotrione

Zhenyuan Xu

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Abstract

3-Chloro-4-methyl-methylsulfonylbenzene,an intermediate of sulcotrione,was synthesized using 4-methylbenzenesulfonyl chloride as a primary material,following by chlorination,reduction and alkylation. The influ-ence on reaction temperature,reaction time,reactant ratio and catalyst was investigatd. The optimum reaction condi-tions are as follows: the chlorinating reaction was carried out at a molar ratio of 4-methylbenzenesulfonyl chloride/ antimony trichloride was 70∶1 and antimony trichloride/iodine was 7∶1 for 3 h at 75-80 °C. The reducting and alkylating reactions were carried out at a molar ratio of sodium sulfite/sodium choloacetate/3-chloro-4-methyl-benzenesulfonyl chloride was 1.1∶1.5∶1 for 4h at 75-80 °C and for 20 h at 103-106 °C respectively with a total yield of 91.2% and a purity of 99.5% in the preparation of 3-chloro-4-methyl-methylsulfonylbenzene.

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3-Chloro-4-methyl-methylsulfonylbenzene,an intermediate of sulcotrione,was synthesized using 4-methylbenzenesulfonyl chloride as a primary material,following by chlorination,reduction and alkylation. The influ-ence on reaction temperature,reaction time,reactant ratio and catalyst was investigatd. The optimum reaction condi-tions are as follows: the chlorinating reaction was carried out at a molar ratio of 4-methylbenzenesulfonyl chloride/ antimony trichloride was 70∶1 and antimony trichloride/iodine was 7∶1 for 3 h at 75-80 °C. The reducting and alkylating reactions were carried out at a molar ratio of sodium sulfite/sodium choloacetate/3-chloro-4-methyl-benzenesulfonyl chloride was 1.1∶1.5∶1 for 4h at 75-80 °C and for 20 h at 103-106 °C respectively with a total yield of 91.2% and a purity of 99.5% in the preparation of 3-chloro-4-methyl-methylsulfonylbenzene.

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Available abstract

3-Chloro-4-methyl-methylsulfonylbenzene,an intermediate of sulcotrione,was synthesized using 4-methylbenzenesulfonyl chloride as a primary material,following by chlorination,reduction and alkylation. The influ-ence on reaction temperature,reaction time,reactant ratio and catalyst was investigatd. The optimum reaction condi-tions are as follows: the chlorinating reaction was carried out at a molar ratio of 4-methylbenzenesulfonyl chloride/ antimony trichloride was 70∶1 and antimony trichloride/iodine was 7∶1 for 3 h at 75-80 °C. The reducting and alkylating reactions were carried out at a molar ratio of sodium sulfite/sodium choloacetate/3-chloro-4-methyl-benzenesulfonyl chloride was 1.1∶1.5∶1 for 4h at 75-80 °C and for 20 h at 103-106 °C respectively with a total yield of 91.2% and a purity of 99.5% in the preparation of 3-chloro-4-methyl-methylsulfonylbenzene.

Key concepts: Chemistry, Molar ratio, Catalysis, Antimony, Yield (engineering), Sodium, Chloride, Nuclear chemistry

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