[CH3:1][C:2]1[CH:3]=[C:4]([C:8](=[O:25])[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[Br:26]Br>C(O)(=O)C>[BrH:26].[Br:26][CH:9]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:24])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:11]=1)[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=1)=[O:25]To a solution of N-[4-[2-(3-methylphenyl)-2-oxoethyl]-2-pyridyl]benzamide (19.0 g, 57.5 mmol) in acetic acid (60 mL) was added dropwise bromine (3.0 mL, 57.5 mmol) at room temperature over 1 hr., and the reaction mixture was stirred for 2 hrs. The precipitated crude crystals were collected by filtration and washed with ethyl acetate to give the title compound (25.4 g, yield 90%).
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