A mild, convenient, and inexpensive procedure for conversion of vinyl halides to α-haloketones

Michael P. VanBrunt, Reuben O. Ambenge, Steven M. Weinreb

Research output: Contribution to journalArticle

44 Scopus citations

Abstract

Treatment of a vinyl chloride with commercially available aqueous sodium hypochlorite solution in a 2:5 mixture of acetic acid/acetone at 0 °C for about 1 h cleanly leads to the corresponding α-chloroketone. Similarly, if a vinyl bromide is exposed to sodium hypobromite (freshly prepared from bromine and sodium hydroxide) at 0 °C in 2:5 acetic acid/acetone as solvent, an α-bromoketone is produced. This methodology has been applied to a number of vinyl chlorides and vinyl bromides, and the transformations generally proceed in high yields. The mild reaction conditions are compatible with a variety of functional groups including amides, esters, and imines.

Original languageEnglish (US)
Pages (from-to)3323-3326
Number of pages4
JournalJournal of Organic Chemistry
Volume68
Issue number8
DOIs
StatePublished - Apr 18 2003

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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