Jump to main content
Jump to site search

Issue 7, 1979
Previous Article Next Article

Electrophilic substitution with rearrangement. Part 8. Some products of bromination of 3,4-dimethylphenol; a route to substitution meta- to a hydroxy-group

Abstract

The brominations of 3,4-dimethylphenol, 2- or 6-bromo-3,4-dimethylphenol, and 2,6-dibromo-3,4-dimethylphenol can lead under defined conditions either to 2,5,6-tribromo-3,4-dimethylphenol or to 2,4,6-tribromo-3,4-dimethyl-cyclohexa-2,5-dienone. The latter compound rearranges to give the former when it is dissolved in concentrated sulphuric acid; and to give 2,6-dibromo-4-bromomethyl-3-methylphenol when it is set aside in the light at room temperature. When 2,5,6-tribromo-3,4-dimethylphenol is heated with concentrated aqueous hydrogen iodide, 5-bromo-3,4-dimethylphenol is obtained; this with bromine gives a mixture of 2,5- and 5,6-dibromo-3,4-di-methylphenol. The mechanisms of these reactions are outlined.

Back to tab navigation

Article type: Paper
DOI: 10.1039/P29790000933
J. Chem. Soc., Perkin Trans. 2, 1979, 933-937

  •   Request permissions

    Electrophilic substitution with rearrangement. Part 8. Some products of bromination of 3,4-dimethylphenol; a route to substitution meta- to a hydroxy-group

    J. M. Brittain, P. B. D. da la Mare, N. S. Isaacs and P. D. McIntyre, J. Chem. Soc., Perkin Trans. 2, 1979, 933
    DOI: 10.1039/P29790000933

Search articles by author

Spotlight

Advertisements