[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[I-:16].[K+].II.Cl>[OH-].[NH4+].O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:9])=[CH:6][C:7]=1[I:16]
A solution of (4-hydroxyphenyl)(phenyl)methanone (2.0 g, 10 mmol) in saturated aqueous ammonium hydroxide (130 mL) was stirred at 25° C. for 15 min, and then treated with a solution of potassium iodide (8.2 g, 49 mmol) and iodine (2.6 g, 10 mmol) in water (260 mL). After 30 min, the mixture was adjusted to pH 2 with concentrated aqueous HCl and extracted with EtOAc (500 mL). The organic extract was sequentially washed with sat. aqueous sodium thiosulfate (100 mL) and brine (100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatographic purification of the residue (ISCO, 40 g, 0->80% EtOAc/hexanes) gave (4-hydroxy-3-iodophenyl)(phenyl)methanone as a white solid. MS (ESI) m/z: Calculated: 324.0; Observed: 325 (M++1).
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