Diethyl Ether → 4-Allyl-2-fluoro-1-triphenylmethylimidazole

Participants

Reaction Steps

To a solution of 2-fluoro-1-triphenylmethylimidazole (1.31 g.) in THF (22 ml.) at -70° under argon was added t-butyl lithium (4 ml. of a 2M solution in pentane). The red solution was stirred at -70° for 2 hours and then cuprous iodide (0.78 g.) added. The resulting dark red solution was stirred at -70° for 1 hour and then allyl bromide (1.8 ml.) added. The mixture was allowed to warm to ambient temperature over 18 hours and then poured into ether (150 ml.). The mixture was washed with saturated aqueous ammonium chloride (6×50 ml.), then brine (50 ml.), treated with charcoal and dried (MgSO4). The solution was evaporated to give 4-allyl-2-fluoro-1-triphenylmethylimidazole as a pale yellow solid, m.p. 136°-138°.

Provenance & Evidence