N(OC(C)(C)C)=O.[Br:8][C:9]1[CH:14]=[CH:13][C:12](N)=[C:11]([I:16])[CH:10]=1.[ClH:17]>C(#N)C.[Cu](Cl)Cl>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:17])=[C:11]([I:16])[CH:10]=1To a stirred suspension of copper (II) chloride (1.62 g, 12.0 mmol) and tert-butyl nitrite (15.0 mmol) in acetonitrile (40 ml), heated at 60° C., was added a solution of 4-bromo-2-iodo-phenylamine (2.98 g, 10.0 mmol) in acetonitrile (10 ml) dropwise over 50 minutes. After stirring at 60° C. for 1 hour, the mixture was poured into 20% hydrochloric acid (200 ml) and extracted with ether (2×30 ml). The crude product was purified by flash chromatography on silica gel eluting with hexane to provide 4-bromo-1-chloro-2-iodo-benzene (2.4 g, 76% yield).
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