[C:1]1([C:7]2[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:8]=2[NH:9]C(=O)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>C(O)C>[C:1]1([C:7]2[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:8]=2[NH2:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=12-Phenyl-4-bromo-N-acetylaniline (7.79 g, 26.85 mmol) was dissolved in ethanol (100 mL), 2 N hydrochloric acid (33.56 mmol, 67.12 mL) was added dropwise under ice bath, and the mixture was heated under reflux overnight. The solution was concentrated under reduced pressure and to the residue were added ethyl acetate (50 mL) and water (40 mL) for extraction. The organic layer was dried over sodium sulfate and, after filtration, concentrated under reduced pressure. The residue was purified by a silica gel column to obtain 2-phenyl-4-bromoaniline (6.58 g).
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