Halogenation of Primary Alcohols Using a Tetraethylammonium Halide/[Et₂NSF₂]BF₄ Combination

Marie-France Pouliot, Olivier Mahé, Jean-Denys Hamel, Justine Desroches and Jean-François Paquin*

*Canada Research Chair in Organic and Medicinal Chemistry, Département de Chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC, Canada G1V 0A6, Email: jean-francois.paquinchm.ulaval.ca

M.-F. Pouliot, O. Mahé, J.-D. Hamel, J. Desroches, J.-F. Paquin, Org. Lett., 2012, 14, 5428-5431.

DOI: 10.1021/ol302496q

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Abstract

The use of a tetraethylammonium halide in the presences of [Et₂NSF₂]BF₄ (XtalFluor-E) enables efficient chlorination and bromination reactions of a wide range of alcohols. Iodination reactions are also possible albeit in lower yields. As opposed to Appel reactions, water-soluble side products are generated, that facilitate work-up.

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Key Words

Bromination, Chlorination

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ID: J54-Y2012-3470