Selectivity in bromination of aromatic substrates by molecular bromine in the presence of reusable zeolites

Bromination of aromatic substrates, namely, toluene, phenol, phenyl acetate and chlorobenzene has resulted predominantly in the formation of para bromo derivatives. While solution bromination of phenyl acetate and chlorobenzene is very slow, zeolite-mediated bromination proceeds smoothly, reflecting the catalytic activity of zeolite in this reaction. A suitable mechanism involving assistance from the sodium ion in generating the active brominating species is proposed. The paraselective bromination of these substrates is also compared with that of nitration and the observed differences are suitably explained.