[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1N.S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:22].[K+]>O>[I:22][C:4]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:3]=1[O:2][CH3:1]2-Methoxy-5-nitroaniline (10.0 g, 0.060 mol) was stirred in water (150 mL) and concentrated (conc.) sulfuric acid (12 mL, 0.22 mol). The solution was cooled below 5° C. with an ice-salt bath, and a solution of sodium nitrite (4.8 g, 0.070 mol) in water (40 mL) was added dropwise while maintaining the temperature below 5° C. A solution of potassium iodide (16.8 g, 0.101 mol) was added and the mixture was heated to 90° C. for 1 hour. Cooling to 0° C. gave dark red crystals which were filtered, washed with water, and dried. Purification by silica gel chromatography using ethyl acetate/hexanes gave the desired compound (13.6 g, 75%). 1H NMR (300 MHz, DMSO-d6): δ 8.57 (s, 1H), 8.28 (d, 1H), 7.19 (d, 1H), 3.98 (s, 3H). LCMS for C7H7INO3 (M+H)+: m/z=280.1.
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