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Brominations of unprotected aromatic amino acids such as phenylalanine, tyrosine, and glycine, with bromoisocyanuric acid mono sodium salt (BICA-Na) were conducted in 60% aq. H(2)SO(4) at 0 degrees C to give a mixture of mono-brominated products in good yield. Unexpectedly, meta-bromophenylglycine was obtained as main product accompanied by ortho- and para-substituted products, while phenylalanine gave only ortho- and para-substituted products. Bromination of 2-phenylethylamine or benzylamine showed a tendency similar to the corresponding amino acids.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Chemistry of Unprotected Amino Acids in Aqueous Solution: Direct Bromination of Aromatic Amino Acids with Bromoisocyanuric Acid Sodium Salt under Strong Acidic Condition