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A User-Friendly Procedure for the Preparation of Secondary Alkyl Chlorides

Gérard Cahiez*, Nicolas Lefèvre, Maël Poizat, Alban Moyeux

*Chimie ParisTech, UMR CNRS 7223, 11 rue Pierre et Marie Curie, 75005 Paris, France, Email: gerard-cahiezchimie-paristech.fr

G. Cahiez, N. Lefèvre, M. Poizat, A. Moyeux, Synthesis, 2013, 45, 231-236.

DOI: 10.1055/s-0032-1317927


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Abstract

A user-friendly exchange reaction enables an efficient preparation of alkyl chlorides in excellent yields from secondary alkyl sulfonates by using benzyltributylammonium chloride in acetone. The reaction tolerates functionalized, base-sensitive and hindered secondary alkyl sulfonates.

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Key Words

nucleophilic substitution, sulfonates, alkyl chlorides, quaternary ammonium halides, sulfonate-halogen exchange


ID: J66-Y2013-0230