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An Efficient Route to Alkyl Chlorides from Alcohols Using the Complex TCT/DMF

Lidia De Luca, Giampaolo Giacomelli* and Andrea Porcheddu

*Dipartimento di Chimica, UniversitÓ degli Studi di Sassari, Via Vienna 2, I-07100 Sassari, Italy, Email: ggpuniss.it

L. de Luca, G. Giacomelli, A. Porcheddu, Org. Lett., 2002, 4, 553-555.

DOI: 10.1021/ol017168p (free Supporting Information)


Abstract

An efficient conversion of alcohols and β-amino alcohols to the corresponding chlorides can be carried out at room temperature in methylene chloride, using 2,4,6-trichloro[1,3,5]triazine and N,N-dimethyl formamide. Addition of NaBr allows the synthesis of bromides. Optically active carbinols react under inversion.

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proposed mechanism



Key Words

alkyl chlorides, benzyl chlorides, alkyl bromides, benzyl bromides


ID: J54-Y2002-640