[C:1]([N:4]1[C:12]2[C:7](=[C:8]([C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[CH3:17])(=[O:3])[CH3:2].[Br:18]Br.C([O-])(O)=O.[Na+]>C(O)(=O)C>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([C:13]([F:16])([F:14])[F:15])[C:9]([Br:18])=[CH:10][CH:11]=2)[CH2:6][CH:5]1[CH3:17])(=[O:3])[CH3:2]To a solution of 1-acetyl-2-methyl-4-(trifluoromethyl)-2,3-dihydro-1H-indole (0.100 g, 0.45 mmol; step A above) in acetic acid (1.0 mL) at rt was added bromine (0.035 mL; 0.68 mmol). More bromine (0.020 mL, 0.39 mmol) was added after 14 h. After another 5 h, the mixture was slowly added to sat'd NaHCO3 and extracted with Et2O (×3). Combined organics were washed (H2O, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.090 g of the title compound as a white solid: MS (ES) m/z 324 (M+2 isomer).
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