Hydrogen Bromide-Acetic Acid Demethylation of 2,3-Dimethoxy-6-bromobenzoic Acid. An Example of Concomitant Bromine Migration1,2

George R. Pettit, David M. Piatak

Research output: Contribution to journalArticlepeer-review

34 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)721-725
Number of pages5
JournalJournal of Organic Chemistry
Volume25
Issue number5
DOIs
StatePublished - Jan 1 1960
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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