Syntheses of 2-(bromodifluoromethyl)benzoxazole and 5-(bromodifluoromethyl)-1,2,4-oxadiazoles

Facile syntheses of CF 2Br-substituted heterocycles are reported. Preparation of 2-(bromodifluoromethyl)benzoxazole ( 2) was achieved in two steps by reaction of 2-aminophenol ( 3) with CF 2BrCO 2Et to give amide ( 4), followed by cyclization of 4 with PPA to give 2. The 5-(bromodifluoromethyl)-1,2,...

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Bibliographic Details
Published in:Journal of fluorine chemistry 1999-06, Vol.95 (1), p.127-130
Main Authors: Dolbier, William R, Burkholder, Conrad R, Médebielle, Maurice
Format: Article
Language:English
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Summary:Facile syntheses of CF 2Br-substituted heterocycles are reported. Preparation of 2-(bromodifluoromethyl)benzoxazole ( 2) was achieved in two steps by reaction of 2-aminophenol ( 3) with CF 2BrCO 2Et to give amide ( 4), followed by cyclization of 4 with PPA to give 2. The 5-(bromodifluoromethyl)-1,2,4-oxadiazoles ( 6a–c) were prepared by one step reaction of amidoximes ( 5a–c) with CF 2BrCO 2Et. These CF 2Br-substituted heterocycles are intermediates in an ongoing investigation of the synthesis of inhibitors of HIV reverse transcriptase having a CF 2 substitution.
ISSN:0022-1139
1873-3328
DOI:10.1016/S0022-1139(99)00007-X