Cl.N[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])=[O:10].N([O-])=O.[Na+].[I:22]I>CC(O)=O.O.CCOC(C)=O>[Cl:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[I:22])=[O:10]
Add concentrated HCl (0.5 mL) to a solution of (2-amino-phenyl)-(2-chloro-phenyl)-methanone (495 mg, 2.14 mmol) in glacial AcOH (1.1 mL). Cool solution to 10° C.; add a solution of sodium nitrite (156 mg, 2.26 mmol) in water (1 mL) dropwise over 30 min. After an additional 30 min., add water (4° C., 2 mL) and EtOAc (4° C., 4 mL). Add a solution of KI (425 mg, 2.56 mmol) and I2 (319 mg, 1.25 mmol) in water (2 mL) dropwise over 25 min. Stir at 5-15° C. for 2.5 hours under N2. Extract with EtOAc (×3), wash with 1N aqueous Na2S2O3 solution (×3), saturated aqueous NaHCO3 solution (×3) and brine. Dry the combined organic layers over Na2SO4 and concentrate. Purify the residue by flash chromatography on silica gel eluting with 0-10% EtOAc/hexanes to afford the title compound (498 mg, 68%): MS(IS) 343 (M+1); TLC (10% EtOAc/hexanes) Rf=0.39.
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