Imidazole → 2-Iodomethyl-1-(4-methoxybenzyloxy)-4-methylbenzene

Participants

Reaction Steps

To a solution of imidazole (1.52 g, 22.32 mmol) and triphenylphosphine (5.85 g, 22.32 mmol) in methylene chloride (30 mL)/THF (15 mL) is added iodine (5.67 g, 22.32 mmol) in portions and the mixture is stirred at RT for 3 h. To this is added dropwise a solution of [2-(4-methoxybenzyloxy)-5-methylphenyl]-methanol (4.80 g, 18.6 mmol) in THF (15 mL) and the mixture is stirred at RT for 18 h. The mixture is concentrated and the insoluble material is filtered. The filtrate is evaporated and the residue is purified by column chromatography using a gradient of 0-75% EtOAc/hexane as eluent to give the title compound as a brown oil.

Provenance & Evidence