Demethylation of 2,3-dimethoxy-6-bromobenzoic acid in hydrogen bromide-acetic acid solution was shown to yield 2,3-dihydroxy-5-bromobenzoic acid. Under similar conditions, 3,4-dimethoxy-6-bromonitrobenzene was found to yield substantial amounts of the unrearranged product of demethylation, 3,4-dihydroxy-6-bromonitrobenzene, accompanied by 3,4-dihydroxynitrobenzene. The structural and environmental features which appear to influence halogen migration in the bromohydroxybenzoic series are summarized.
ASJC Scopus subject areas
- Organic Chemistry