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A Highly Chemoselective and Rapid Chlorination of Benzyl Alcohols under Neutral Conditions

Lili Sun, Guisheng Peng, Hongmei Niu, Qiang Wang, Chunbao Li*

*Department of Chemistry, College of Science, Tianjin University, Tianjin 300072, P. R. of China, Email:

L. Sun, G. Peng, H. Niu, Q. Wang, C. Li, Synthesis, 2008, 3919-3924.

DOI: 10.1055/s-0028-1083243


A rapid, selective, and high-yielding chlorination of benzylic alcohols in the presence of 2,4,6-trichloro-1,3,5-triazine and dimethyl sulfoxide takes 10 to 40 minutes. The neutral reaction conditions are compatible with substrates bearing acid-labile functional groups. Both competitive intramolecular and intermolecular reactions for benzyl alcohols in the presence of aliphatic alcohols indicate high selectivity.

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proposed mechanism

Key Words

benzyl alcohols, benzyl chlorides, chemoselectivity, halogenation, sulfoxides

ID: J66-Y2008-3720