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Facile Approach to Geminal Heterodihalogenation. One-Pot Synthesis of α-Bromo-α-Chloro Ketones
Synlett ( IF 2 ) Pub Date : 2020-07-01 , DOI: 10.1055/s-0040-1707169
Ming Bian 1 , Jin-feng Zhou , Dong-min Tang
Affiliation  

An efficient and practical protocol for the geminal heterodihalogenation of methyl ketones by using readily available dimethyl sulfoxide and a combination of HCl and HBr is reported. Control experiments suggested that the acidity of the solution, as well as the oxidizing ability and nucleophilicity of the dimethyl sulfoxide might work cooperatively in ensuring the success of the tandem substitution. Its operational simplicity, easy accessibility, and mild oxidative conditions suggest that the present strategy might be useful for the assembly of bromochloromethyl functional groups in drug discovery.

中文翻译:

Geminal 异二卤化的简便方法。α-溴-α-氯酮的一锅法合成

报告了使用现成的二甲基亚砜和 HCl 和 HBr 的组合对甲基酮进行孪生异二卤化的有效和实用的协议。对照实验表明,溶液的酸度以及二甲基亚砜的氧化能力和亲核性可能协同工作以确保串联取代的成功。其操作简单、易于访问和温和的氧化条件表明,本策略可能有助于药物发现中溴氯甲基官能团的组装。
更新日期:2020-07-01
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