Synthesis

A New Approach to the Synthesis of 2-Aryl-4-halomethyl-5-methyl-1, 3-oxazoles by Highly Regioselective Direct Halogenation with NBS or NCS/MeCN

T Yamane, H Mitsudera, T Shundoh

Index: Yamane, Taihei; Mitsudera, Hiroyuki; Shundoh, Takatsugu Synthesis, 2004 , # 17 p. 2825 - 2832

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Citation Number: 4

Abstract

Abstract A simple and efficient method for the synthesis of 2-aryl-4-bromomethyl-5-methyl-1, 3-oxazoles 2 and 2-aryl-4-chloromethyl-5-methyl-1, 3-oxazoles 3 is described. The reaction of 2-aryl-4, 5-dimethyl-1, 3-oxazoles 1 with N-bromosuccinimide and N-chlorosuccinimide in acetonitrile under mild conditions provides 4-halomethyl isomers with exceptionally high regioselectivity in moderate to good yields.