ipso Halogenation. II. Bromination of phenols, isomerization and disproportionation of bromophenols, and dienone-phenol rearrangement of bromodienones

A Fischer, GN Henderson

Index: Fischer, Alfred; Henderson, George Narayanan Canadian Journal of Chemistry, 1983 , vol. 61, p. 1045 - 1052

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Citation Number: 22

Abstract

Bromination of p-cresol, 2-bromo-p-cresol, 3, 4-dimethylphenol, and mesitol in trifluoromethanesulfonic acid gives as the main product the bromo derivative with bromine meta to hydroxyl, a result attributed to the intermediate formation of a bromodienone and its rearrangement. Phenol does not give m-bromophenol in trifluoromethanesulfonic acid. 4- Bromo-2, 4, 6-trimethylcyclohexa-2, 5-dienone rearranges to 3-bromomesitol in ...