N[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[OH:9].N([O-])=O.[Na+].[I-:14].[K+]>CS(C)=O.O.OS(O)(=O)=O.O.C(OCC)(=O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([I:14])=[C:3]([OH:9])[CH:4]=12-Amino-5-chlorophenol (5.7 g, 40 mmol) is dissolved in DMSO/water/H2SO4 (200/60/140 mL) and cooled to 0° C. To this solution is added sodium nitrite (4.1 g, 60 mmol) in water (20 mL) and the mixture is stirred for 1 h at 0° C. To the mixture is added potassium iodide (19.9 g, 120 mmol) in water (20 mL) and the mixture is stirred at room temperature for 1 h. Another batch of potassium iodide (19.9 g, 120 mmol) in water (20 mL) is added and the mixture is stirred at room temperature for 1 h. The mixture is diluted with ethyl acetate, washed with water, saturated aqueous sodium sulfate, and brine. The organic portion is dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (Biotage™ Si65M, 20% ethyl acetate/hexane) to yield 8.09 g (79%) of the title compound as a pink solid. GCMS m/e 254 [M]−.
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