B(O[O-])=O.[Na+].[I-:6].[K+].S(=O)(=O)(O)O.[C:13]([C:15]1[CH:20]=[CH:19][C:18]([NH:21]C(=O)C)=[C:17]([F:25])[CH:16]=1)#[N:14].S([O-])([O-])(=O)=S.[Na+].[Na+].S(=O)(O)[O-].[Na+]>C(O)(=O)C.C(OC(=O)C)(=O)C.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[NH2:21][C:18]1[C:19]([I:6])=[CH:20][C:15]([C:13]#[N:14])=[CH:16][C:17]=1[F:25]A solution of sodium perborate (4.2 g, 27.3 mmols) and sodium tungstate (450 mg, 1.4 mmol) in a mixture of 20 mL of glacial acetic acid and 15 mL of acetic anhydride was treated with a solution of potassium iodide (2.3 g, 13.9 mmols) in 15 mL of water. The mixture was treated with 7.5 mL of concentrated sulfuric acid over 15 minutes. A suspension of N-(4-cyano-2-fluorophenyl)acetamide (1.79 g, 10 mmols) in 15 mL of glacial acetic acid was added to and the resulting mixture was heated at 50° C. After 1 hour, the mixture was poured into 300 mL of crushed ice and treated with 100 mL of a saturated solution of sodium thiosulfate followed by 100 mL of a sodium bisulfite solution. The mixture was extracted with three 100 mL portions of dichloromethane and the combined organic layers were washed with three 50 mL portions of sodium bicarbonate solution, three 50 mL portions of water, dried over sodium sulfate, and concentrated in vacuo to give a light brownish solid. Chromatography on SiO2 (50% ethyl acetate in hexanes) afforded 400 mg of the title product as a light brownish solid (15% yield).
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