Advances in the synthesis and applications of organobromine compounds

Bromination of toluene in quantitative yield and with excellent para-selectivity can be achieved by use of tert-butyl hypobromite in the present of proton-exchanged zeolite X. Highly para-selective bromination of phenols is possible with a polystyrene resin bearing tetraalkylammonium tribromide groups. Bromocompounds produced in these or other ways are useful as substrates either in direct substitution reactions or via conversion into organometallic reagents and subsequent reactions with electrophiles. Interesting examples include the syntheses of diaryl ethers, highly hindered organoboron compounds, and indigo and related compounds