A mild, convenient, and inexpensive procedure for conversion of vinyl halides to alpha-haloketones.
Treatment of a vinyl chloride with commercially available aqueous sodium hypochlorite solution in a 2:5 mixture of acetic acid/acetone at 0 degrees C for about 1 h cleanly leads to the corresponding alpha-chloroketone. Similarly, if a vinyl bromide is exposed to sodium hypobromite (freshly prepared from bromine and sodium hydroxide) at 0 degrees C in 2:5 acetic acid/acetone as solvent, an alpha-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.
VanBrunt
Michael P
MP
Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA. smw@chem.psu.edu
Ambenge
Reuben O
RO
Weinreb
Steven M
SM
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007659:Ketones / Q000138:chemical synthesis*; D015394:Molecular Structure; D012973:Sodium Hypochlorite / Q000737:chemistry; D013696:Temperature; D013997:Time Factors; D014753:Vinyl Compounds / Q000737:chemistry*
D006846:Hydrocarbons, Halogenated; D007202:Indicators and Reagents; D007659:Ketones; D014753:Vinyl Compounds; D012973:Sodium Hypochlorite