Regiospecific incorporation of bromine and iodine into phenols using (trimethylsilyl)phenol derivatives was written by Wilbur, D. S.;Stone, W. E.;Anderson, K. W.. And the article was included in Journal of Organic Chemistry in 1983.Computed Properties of C8H7BrO2 This article mentions the following:
An investigation of regiospecifically halogenating (and radiohalogenating) phenolic rings was carried out. The investigation used (trimethylsilyl)phenols, (trimethylsilyl)anisoles, and (trimethylsilyl)phenyl acetates as model compounds Brominations and iodinations of these compounds were carried out in MeOH or HOAc by generating the brominating agent (BrCl) or iodinating agent (ICl) in situ from the halide salts and N-chlorosuccinimide. None of the (trimethylsilyl)phenols yielded exclusive bromination by ipso substitution of the trimethylsilyl group. Of the (trimethylsilyl)anisoles, the ortho and para isomers gave regiospecific replacement of the trimethylsilyl group. All of the (trimethylsilyl)phenyl acetates yielded completely regiospecific incorporation of bromine and iodine by ipso substitution of the trimethylsilyl group. Yields of 80-90% were obtained for the halogenations (and radiohalogenations). In the experiment, the researchers used many compounds, for example, 3-Bromophenyl acetate (cas: 35065-86-2Computed Properties of C8H7BrO2).
3-Bromophenyl acetate (cas: 35065-86-2) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Computed Properties of C8H7BrO2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary