Imidazole → Iodomethylcycloheptane

Participants

Reaction Steps

To a stirred solution of triphenylphosphine (24.59 g; 92.8 mmol) and imidazole (6.40 g; 93.1 mmol) in methylene chloride (100 mL) cooled to 0° C. and Iodine (23.52 g; 92.7 mmol) was added portionwise over a 10 minute period. A solution of cycloheptane methanol (9.14 g; 71.3 mmol) dissolved in methylene chloride (50 mL) was then added over a 5 minute period. The cooling bath was removed and the mixture allowed to warm to room temperature and stirred overnight. The mixture was diluted with methylene chloride, washed with water and the organic layer dried (magnesium sulfate), filtered and concentrated in vacuo. The crude product was chromatographed (eluent:hexanes) to give 15.35 g (93%) of cycloheptylmethyl iodide as an oil.

Provenance & Evidence