Iodine → 4-Chlorophenethyl iodide

Participants

Reaction Steps

A solution of O-phenylene phosphorochloridite (10.12 g, 58 mmol) and pyridine (4.6 g, 58 mmol) in diethyl ether (200 mL) is cooled to 0° C. and treated dropwise with a solution of 4'-chlorophenethyl alcohol (9 g, 57.5 mmol) in diethyl ether (100 mL) and stirred 2 days. The resulting pyridine hydrochloride is collected by filtration and the filtrate is concentrated under vacuum to an oil. A solution of the oil in dichloromethane (150 mL) is stirred 10 days with iodine (14.72 g, 58 mmol) and then the reaction mixture is washed successively with 5% sodium hydroxide solution, 5% sodium bisulfite solution, and then saturated sodium chloride solution. The dried (MgSO4) organic layer is concentrated in vacuo to provide 17.1 g of a pale yellow oil whose proton nuclear magnetic resonance (PMR) spectrum is consistent with its structure.

Provenance & Evidence