THE ORTON REARRANGEMENT IN APROTIC SOLVENTS: PART II. THE ACID-CATALYZED BROMINATION OF ANISOLE BY A SERIES OF 4-SUBSTITUTED N-BROMOACYLANILIDES

Abstract

Anisole has been brominated using a sequence of brominating reagents generated by the reaction of a series of 4-substituted N-bromoacylanilides 4-RC6H4NBrAc (R = Ph, H, Cl, and NO2) with a series of carboxylic acids R′COOH (R′ = CF3, CCl3, CH2Cl, and CH3). The isomer distributions of the bromoanisoles produced have been measured for each N-bromoacylanilide–carboxylic acid pair and their variation with both the structure of the N-bromoacylanilide and the carboxylic acid provides a useful basis for a discussion of the mechanism of the bromine migration.