[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([I:9])[CH:3]=1.[C:10]1([S:16](Cl)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N([CH2:25][CH3:26])CC)C>ClCCl.C(=O)(O)[O-].[Na+]>[C:10]1([S:16]([N:6]([S:16]([C:26]2[CH:25]=[CH:12][CH:11]=[CH:10][CH:15]=2)(=[O:18])=[O:17])[C:5]2[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][C:4]=2[I:9])(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1A solution of 4-bromo-2-iodoaniline (8.5 g, 28.5 mmol) in 200 mL of dichloromethane was sequentially treated with benzenesulfonyl chloride (15 mL, 117.5 mmol) and triethylamine (25 mL, 179.6 mmol). After 4 days, the mixture was diluted with 100 mL of saturated aqueous sodium bicarbonate solution and extracted with three 100 mL portions of ethyl acetate. The combined organic layers were washed with 50 mL of brine, three 60 mL portions of saturated aqueous ammonium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was triturated with diethyl ether to afford 5.74 g (35% yield) of N,N-bisbenzenesulfonyl-(4-bromo-2-iodoaniline).
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