Electrophilic substitution with rearrangement. Part 10. Some products of bromination of 2.4-dimethylphenol and of 4-t-butyl-2- methylphenol

Abstract

The reaction of 2,4-dimethylphenol with bromine gives first 6-bromo-2,4-dimethylphenol, which according to the conditions of further bromination can give 4,6-dibromo-2,4-dimethylcyclohexa-2,5-dienone; a mixture of 5,6with some 3,6-dibromo-2,4-dimethylphenol; 6-bromo-4-bromomethyl-2-methylphenol with none of the 2-bromomethyl-4-methyl isomer; or a mixture from which 6-bromo-2,4-bis(bromomethyl)phenol can be isolated. The corresponding dienone from 6-bromo-4-t-butyl-2-methylphenol reacts by more complex pathways, and the products include those of de-t-butylation. The probable mechanisms involved in these reactions are discussed.