[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:10])([CH3:3])[CH3:2].C([O-])(=O)C.[Na+].[Cl-].[I-:17]>C(O)(=O)C.C(OCC)(=O)C>[I:17][C:8]1[CH:7]=[CH:6][C:5]([NH2:10])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:9]=1To a solution of 2-isopropyl-phenylamine (262 mg, 1.94 mmol) and sodium acetate (159 mg, 1.94 mmol) in 5 mL acetic acid, was added iodide monochloride (409 mg, 2.58 mmol) at room temperature. The mixture was stirred at room temperature for 20 minutes, then diluted with ethyl acetate and washed with saturated sodium bicarbonate. The organic layers were combined and concentrated in vacuo to give a crude residue, which was purified by column chromatography (silica 5-25% EtOAc/hexane) to give 4-iodo-2-isopropyl-phenylamine.
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