Potassium Iodide → 1,4-Bis(trifluoromethyl)-2,5-diiodobenzene

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To a solution of 30 mL H2SO4 was added periodic acid (3.18 g, 14 mmol) and potassium iodide (6.90 g, 42 mmol) under ice bath and then 1,4-bis(trifluoromethyl)benzene (2.17 mL, 14 mmol) was added. The reaction mixture was then stirred at 70° C. for 5 h. After cooling down to room temperature, the resulting solution was poured into ice-water and then extracted with diethyl ether (100 mL) and 10% sodium thiosulfate (50 mL). The organic layer was washed with 10% sodium thiosulfate (3×50 mL), dried over MgSO4, filtered, and concentrated. The residue was recrystallized from hexane to give 19 as a white solid (4.24 g, 65%): 1H NMR (300 MHz, CDCl3): δ 8.20 (s, 2H); 19F N (282 MHz, CDCl3): −64.2; HR-MS (EI) calcd. for C8H2F6I2 (M+): 465.81, found: 465.8387.

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