title: Chemistry of unprotected amino acids in aqueous solution: direct bromination of aromatic amino acids with bromoisocyanuric acid sodium salt under strong acidic condition.
abstract: 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.
authors.affiliation: Department of Pharmaceutical Sciences, Toho University. yokoyama@phar.toho-u.ac.jp
authors.forename: Yuusaku
authors.initials: Y
authors.lastname: Yokoyama
authors.forename: Tomotsugu
authors.initials: T
authors.lastname: Yamaguchi
authors.forename: Masanori
authors.initials: M
authors.lastname: Sato
authors.forename: Eri
authors.initials: E
authors.lastname: Kobayashi
authors.forename: Yasuoki
authors.initials: Y
authors.lastname: Murakami
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Okuno
mesh_terms: D024322:Amino Acids, Aromatic / Q000737:chemistry*; D001966:Bromine / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D014227:Triazines / Q000737:chemistry*
chemical_list: D024322:Amino Acids, Aromatic; D014227:Triazines; C516817:bromoisocyanuric acid; D001966:Bromine