Imidazole → 4-(2-iodoethyl)phenol

Participants

Reaction Steps

Triphenylphosphine (1.57 g, 0.006 mol) and imidazole (0.41 g, 0.006 mol) were added to dry dichloromethane (20 ml). When the imidazole was in solution iodine (1.52 g, 0.006 mol) was added. After precipitation of the imidazole hydroiodide (4-hydroxyphenethyl) alcohol (0.69 g, 0.005 mol) was added. The mixture was stirred at room temperature for 4 h. Then water was added and the mixture was extracted with dichloromethane. The extracts were washed with water, dried and concentrated in vacuo to give a raw product. Purification by flash chromatography (heptane/ethyl acetate as a gradient eluent 9:1-6:4) gave a pure product. 1H NMR (400 MHz, DMSO-d6): 2.99 (2H, t, 3J=7.6 Hz), 3.38 (2H, t, 3J=7.6 Hz), 6.68 (2H, d, 3J=8.5 Hz), 7.03 (2H, d, 3J=8.5 Hz), 9.24 (1H, s, —OH).

Provenance & Evidence