Imidazole → 1-(2-Iodoethyl)-4-nitrobenzene

Participants

Reaction Steps

To a 0° C. solution of triphenylphosphine (1.9 g, 7.2 mmol) and imidazole (489 mg, 7.18 mmol) in DCM (20 ml) was added iodine (1822 mg, 7.18 mmol) to form a solution. Small portions of 2-(4-nitrophenyl)ethanol (1.0 g, 6.0 mmol) was added to the suspension. TLC showed conversion to the desired product quickly. Hexane was added to the reaction to precipitate side products which were filtered off. The filtrate was concentrated in vacuo to obtain crude 1-(2-iodoethyl)-4-nitrobenzene, which was purified by silica gel flash chromatography using Hexane and EtOAc system. 1H-NMR (500 MHz, CD3Cl) δ 8.22 (d, J=8.5 Hz, 2H), 7.40 (d, J=8.5 Hz, 2H), 3.41 (t, J=7.0 Hz, 2H), 3.32 (t, J=7.0 Hz, 2H).

Provenance & Evidence