[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[C:9]([F:12])([F:11])[F:10])N.C1(C)C=CC(S(O)(=O)=O)=CC=1.[I-:24].[K+].N([O-])=O.[Na+].C([O-])(O)=O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CC#N.O>[Cl:1][C:2]1[CH:3]=[C:4]([I:24])[CH:6]=[CH:7][C:8]=1[C:9]([F:12])([F:11])[F:10]To a solution of 3-chloro-4-(trifluoromethyl)aniline (450 mg, 2.30 mmol) and toluene 4-sulfonic acid (1.19 g, 6.92 mmol) in CH3CN (10 mL) was added a solution of potassium iodide (955 mg, 5.76 mmol) and sodium nitrite (318 mg, 4.61 mmol) in water (1.8 mL) over 15 min at 10° C., then after 20 min the reaction mixture was poured onto water, neutralized with sat. aq. NaHCO3 solution, treated with 2 M aq. sodium thiosulfate solution (6 mL), and extracted with EtOAc. The organic layer was dried (MgSO4), filtered, and evaporated to afford the title compound (517 mg) as a light brown oil, which was directly used in the next step.
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