Synthesis ( IF 2.2 ) Pub Date : 2019-08-22 , DOI: 10.1055/s-0039-1690617 Shuai Shuai Huang , Zhan Jiang Zheng 1 , Yu Ming Cui , Zheng Xu , Ke Fang Yang , Li Wen Xu 1
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Abstract
A convenient and efficient three-step synthesis of 2-(2,2-difluoroethoxy)-6-(trifluoromethyl)benzenesulfonyl chloride, the key building block of penoxsulam, is described. The main features of the synthesis include a regioselective lithiation and subsequent electrophilic substitution starting from commercially available 3-bromobenzotrifluoride to provide (2-bromo-6-(trifluoromethyl)phenyl)(propyl)sulfane, then a copper-catalyzed C–O coupling to introduce the difluoroethoxy moiety and chloroxidation conditions to give the desired sulfonyl chloride.
A convenient and efficient three-step synthesis of 2-(2,2-difluoroethoxy)-6-(trifluoromethyl)benzenesulfonyl chloride, the key building block of penoxsulam, is described. The main features of the synthesis include a regioselective lithiation and subsequent electrophilic substitution starting from commercially available 3-bromobenzotrifluoride to provide (2-bromo-6-(trifluoromethyl)phenyl)(propyl)sulfane, then a copper-catalyzed C–O coupling to introduce the difluoroethoxy moiety and chloroxidation conditions to give the desired sulfonyl chloride.
中文翻译：
便捷合成2-（2,2-二氟乙氧基）-6-（三氟甲基）-苯磺酰氯，一种五氧化二Key的重要组成部分
抽象的
描述了一种便捷有效的三步合成2-（2,2-二氟乙氧基）-6-（三氟甲基）苯磺酰氯的方法。合成的主要特征包括区域选择性锂化和随后的亲电取代，从市售的3-溴三氟甲苯开始提供（2-溴-6-（三氟甲基）苯基）（丙基）硫烷，然后通过铜催化的C-O偶联至引入二氟乙氧基部分和氯氧化条件，得到所需的磺酰氯。
描述了一种便捷有效的三步合成2-（2,2-二氟乙氧基）-6-（三氟甲基）苯磺酰氯的方法。合成的主要特征包括区域选择性锂化和随后的亲电取代，从市售的3-溴三氟甲苯开始提供（2-溴-6-（三氟甲基）苯基）（丙基）硫烷，然后通过铜催化的C-O偶联至引入二氟乙氧基部分和氯氧化条件，得到所需的磺酰氯。
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