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The Use of Bromotrichloromethane in Chlorination Reactions

Stephen G. Newman, Christopher S. Bryan, Didier Perez, Mark Lautens*

*Department of Chemistry, University of Toronto, Toronto, ON, M5S 3H6, Canada, Email: mlautenschem.utoronto.ca

S. G. Newman, C. S. Bryan, D. Perez, M. Lautens, Synthesis, 2011, 342-346.

DOI: 10.1055/s-0030-1258368 (free Supporting Information)


Abstract

Stoichiometric bromotrichloromethane in acetonitrile can replace solvent quantities of carbon tetrachloride in the synthesis of gem-dichloroalkenes from aldehydes in the presence of triphenylphosphine. Similarly, bromotrichloromethane in dichloromethane can be used for the Appel reaction of benzyl alcohols to form benzyl chlorides at r.t., which is commonly carried out in refluxing carbon tetrachloride.

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Key Words

olefination, aldehydes, halogenation, Appel reaction, benzyl halides


ID: J66-Y2011-0160