Imidazole → 5-Bromo-2-[2-(3-methoxy-2-methylphenyl)-ethyl]-phenyliodomethane

Participants

Reaction Steps

To polymer-supported triphenylphosphine (9.2 g; ˜27.5 mmol) in dichloromethane (40 mL) was added iodine (6.98 g; 27.5 mmol). The mixture was stirred for 30 minutes and then imidazole (1.87 g; 27.5 mmol) was added to the mixture. After stirring for 15 minutes a solution of 5-bromo-2-[2-(3-methoxy-2-methylphenyl)-ethyl]-phenylmethanol 8 (4.19 g; 12.5 mmol) in dichloromethane (100 mL) was added. The mixture was heated at reflux for 2 hours, cooled to room temperature and filtered. The filtrate was washed sequentially with sodium thiosulfate solution, water, and brine, dried over MgSO4, and concentrated to dryness at ambient temperature under high vacuum to give compound 9 as a yellow oil, 5.56 g.

Provenance & Evidence