[Cl:1][C:2]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:3]=1N.N([O-])=O.[Na+].[I-:17].[K+].Cl>C(#N)C>[Cl:1][C:2]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:3]=1[I:17]A solution of 2-chloro-4-(methanesulfonyl)aniline (25 g, 122 mmol) in acetonitrile (500 mL) was cooled to 0° C., then sodium nitrite (20.97 g, 303.9 mmol) and potassium iodide (50.45 g, 303.9 mmol) were added. After the reaction mixture was stirred for 30 minutes at 0° C., concentrated hydrochloric acid (50 mL) was added drop-wise via an addition funnel. The reaction was stirred at 0° C. for an additional 45 minutes. The reaction mixture was warmed to room temperature, then stirred for 2.5 hours. The reaction mixture was poured into ice water (800 mL), and extracted with dichloromethane. The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated. Flash chromatography (RediSep® Flash column, 230-400 mesh, 10%-35% ethyl acetate in hexane) gave 2-chloro-1-iodo-4-methanesulfonyl-benzene (13.88 g, 36%). 1H NMR (300 MHz, CDCl3) δ ppm 8.11 (d, J=8.4 Hz, 1 H), 8.00 (d, J=1.9 Hz, 1 H), 7.51 (dd, J=8.4, 1.9 Hz, 1 H), 3.07 (s, 3 H).
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