Facile Approach to Geminal Heterodihalogenation. One-Pot Synthesis of α-Bromo-α-Chloro Ketones

Synlett DOI: 10.1055/s-0040-1707169 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. [...] © Georg Thieme Verlag Stuttgart · New YorkArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synlett - June 30, 2020 Category: Chemistry Authors: Zhou, Jin-feng Tang, Dong-min Bian, Ming Tags: letter Source Type: research