Iodine → 3-Iodo-4-propylbenzoic acid

Participants

Reaction Steps

A mixture of 4-propylbenzoic acid (0.3 g; 1.83 mmol), CF3SO3Ag (0.47 g; 1.83 mmol) and I2 (0.46 g; 1.83 mmol) in CH2Cl2 was stirred for 48 h at room temperature, then filtered through Celite pad, washed with fresh CH2Cl2 (2×15 ml). The combined filtrates were washed with 5% NaHSO3, H2O, brine, dried over anhydrous MgSO4, filtered and filtrate evaporated under reduced pressure to give the title compound (0.49 g; 92%) as creamy solid. 1H-NMR (CDCl3) 1.0 (tr, 3H, J=9 Hz); 1.57-1.7 (m, 2H); 1.72-1.77 (m, 2H); 7.28 (d, 1H, 9 Hz); 7.98 (dd, 1H, J=3, 6 Hz); 8.53 (d, 1H, J=3 Hz).

Provenance & Evidence