[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:13])=[C:7]([NH:9][C:10](=[O:12])[CH3:11])[CH:8]=1.[Br:14]Br>C(O)(=O)C>[Br:14][C:4]1[C:3]([O:2][CH3:1])=[CH:8][C:7]([NH:9][C:10](=[O:12])[CH3:11])=[C:6]([CH3:13])[CH:5]=1To a solution of N-(5-methoxy-2-methylphenyl)acetamide in acetic acid (40 mL) was added Br2 (3 g, 19 mmol) slowly. The mixture was capped and stirred at 50° C. for 5 hours. The reaction was cooled to room temperature, then quenched with sodium sulfite aqueous solution, and extracted with ethyl acetate (3×50 mL). The combined organic layer was dried over Na2SO4 and concentrated to give crude N-(4-bromo-5-methoxy-2-methylphenyl)acetamide as a brown oil, which was used in the next step without further purification.
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