Imidazole → HCID 89544426, compound

Participants

Reaction Steps

500 mg of [1-[3-chloro-5-(trifluoromethyl)-2-pyridyl]cyclopropyl]methanol (step 2) was dissolved in 20 ml dichloromethane and the solution was cooled in an ice bath. Then 560 mg triphenylphosphine and 150 mg imidazole were added. When a clear solution had formed, 550 mg iodine was added in portions. The reaction was stirred at ambient temperature overnight. The mixture was diluted with dichloromethane, washed with a saturated solution of sodium thiosulfate and the organic phase was concentrated. The residue was triturated with 30 ml of hexane. The solid was removed by filtration and the filtrate was concentrated. The residue was purified on 20 g of silica gel, eluent hexane/ethyl acetate (20:1). Thus, 610 mg of 3-chloro-2-[1-(iodomethyl)cyclopropyl]-5-(trifluoromethyl)pyridine was obtained as a pale yellow oil. 1H-NMR (CDCl3): 8.76 ppm (s, 1H), 7.93 ppm (s, 1H), 3.61 ppm (s, 2H), 1.49 ppm (m, 2H), 1.17 ppm (m, 2H).

Provenance & Evidence