Synthetic communications

A one-pot method for the efficient conversion of aryl-and acyl-substituted methyl alcohols into chlorides

G Lai, PZ Tan, P Ghoshal

Index: Lai, Gaifa; Tan, Ping-Zhong; Ghoshal, Pallab Synthetic Communications, 2003 , vol. 33, # 10 p. 1727 - 1732

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Citation Number: 9

Abstract

Abstract A one-pot and efficient conversion of aryl-and acyl-substituted methyl alcohols into the corresponding chlorides is described, which involved tosylation with tosyl chloride and triethylamine in the presence of a catalytic amount of 4-(dimethylamino) pyridine (DMAP) in CH2Cl2, followed by methanol-facilitated replacement of the tosylates with chloride. This mild method is readily amenable to large-scale synthesis.