A Mild, Convenient, and Inexpensive Procedure for Conversion of Vinyl Halides to α-Haloketones.

✍ Scribed by Michael P. VanBrunt; Reuben O. Ambenge; Steven M. Weinreb

• Publisher: John Wiley and Sons
• Year: 2003
• Weight: 151 KB
• Volume: 34
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.200333047

✦ Synopsis

A Mild, Convenient, and Inexpensive Procedure for Conversion of Vinyl Halides to α-Haloketones. -Reaction of vinyl chlorides (I) with sodium hypochlorite in acidic solution provides an efficient access to α-chloroketones (II). Analogously, the vinyl bromides react with freshly prepared sodium hypobromite to afford α-bromoketones in good yields. The reaction proceeds under mild conditions and tolerates a variety of functional groups like esters, amides and imines. The reaction of vinyl chlorides with NaOBr or vice versa can lead to mixtures of α-chloroketones and α-bromoketones. The ratio is supposed to be determined by the ability of in situ generated bromonium ions to convert into chloronium ions and vice versa. -(VANBRUNT, M.