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

doi:10.1039/P29790000933

Paper

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

Published Oct 9, 1979 · J. M. Brittain, Peter B. D. da la Mare, N. Isaacs

Journal of The Chemical Society-perkin Transactions 1

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2

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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.

Study Snapshot

Bromination of 3,4-dimethylphenol can lead to 2,5,6-tribromo-3,4-dimethylphenol or 2,4,6-tribromo-3,4-dimethyl-cyclohexa-2,5-dienone, with various rearrangements.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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

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