A solution of C10F21I (4.2 g, 6.5 mmol) was added dropwise over 10 min to a stirred mixture of 2-bromo-p-xylene (1 g, 5.4 mmol), copper powder (1.9 g, 29.7 mmol), and DMSO (80 mL) at 130° C. The reaction mixture was subsequently stirred for a further 2 d at this temperature. After cooling to room temperature, it was poured into a beaker containing dichloromethane (50 mL) and saturated potassium iodide solution (50 mL). After filtering, the organic layer was separated, washed with water (3×30 mL), and dried over MgSO4. Recrystallization from hexane gave the product 215 as a white solid (2.7 g, 82%): 1H NMR (300 MHz, CDCl3): 7.31 (1H, s), 7.24 (1H, d, J=8.1 Hz)), 7.17 (1H, d, J=8.1 Hz)), 2.46 (3H, t, J=3.0 Hz)), 2.39 (3H, s); 19F NMR (282 MHz, CDCl3): −81.4, −106.7, −121.1, −121.8, −122.0, −122.9, −126.3; HR-MS (EI) calcd. for C18H9F21 (M+): 624.0363, found: 624.0353.
