[Cl:1][C:2]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:3]=1N.Cl.N([O-])=O.[Na+].[I-:18].[K+]>O.C(O)(=O)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:18]2-Chloro-4-Methylsulfonylaniline in a 1:1:3 mixture (0.4 M) of Acetic Acid, Hydrochloric Acid, 37% and Water was cooled to 0° C. and slowly treated with a 4 M solution of sodium nitrite in water. The reaction was stirred at 5° C. for 30 minutes then treated dropwise with a 2M solution of potassium iodide in water. The reaction evolved a gas and turned brown. The reaction was stirred 15 minutes at 0° C., 40 minutes at rt and 1 h at 60° C. The brown solid was filtered, dissolved in ethyl acetate and the solution washed with acidified sodium thiosulfate and then brine. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. During evaporation, a precipitate appeared and was filtered. The mother liquors were evaporated further and 2 more crops were collected. The last mother liquor was transferred with diethyl ether and upon evaporation yields more products.
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