Sodium Iodide → 4-Iodophenylsulfur Pentafluoride

Participants

Reaction Steps

Sodium iodide (5.5 mg, 0.037 mmol) was added portion-wise to a solution of 1 (9.9 mg, 0.031 mmol) and p-xylene (60.1 mg, 0.566 mmol) in CH3CN (0.11 g). The reaction mixture was filtered through Celite 545 using CH2Cl2. The solvent was evaporated to give a brown oil, which was purified by SiO2 column chromatography with hexane to afford 25b (1.4 mg, 14%) and 28b as a colorless oil (1.3 mg, 14%): MS (GC, EI): m/z=308 [M+], 181 [M+-SF5]. IR (ATR): {tilde over (v)}=2924, 1599, 1493, 1456, 1395, 1099, 833 cm−1. 1H NMR (500 MHz, CDCl3): δ=7.79 (d, J=8.5 Hz, 2H), 7.40 (d, J=8.5 Hz, 2H), 7.18 (d, J=8.3 Hz, 1H), 7.12 (d, J=8.3 Hz, 1H), 7.02 (s, 1H), 2.36 (s, 3H), 2.22 (s, 3H) ppm. 13C NMR (125 MHz, CDCl3): δ=155.0 (C), 145.6 (C), 139.5 (C), 132.0 (C), 130.5 (CH), 130.2 (CH), 129.4 (2CH), 128.8 (CH), 125.7 (2CH), 20.9 (CH3), 19.8 (CH3) ppm. 19F NMR (470 MHz, CDCl3): δ=84.9 (quint, J=150 Hz, 1 F), 63.2 (d, J=150 Hz, 4 F) ppm.

Provenance & Evidence