Carbon tetrabromide → HCID 15752645, compound

Participants

Reaction Steps

A mixture of 2-(cyclohexyloxy)ethanol (0.5 g, 3.47 mmol), carbon tetrabromide (1.49 g, 4.51 mmol), and dichloromethane (6 mL) was placed in a 20 mL scintillation vial with a magnetic stirring bar and cooled on an ice-water bath. Triphenylphosphine (1.18 g, 4.51 mmol) was added in three portions over 5 min with stirring. The mixture was allowed to warm to ambient temperature and progress was monitored with TLC using ethyl acetate:hexanes (1:1) (Rf starting material=0.6, Rf product=0.9). The mixture was concentrated under reduced pressure. Hexanes (5 mL) and ethyl ether (10 mL) were added twice and removed by decanting, leaving an oily residue that was purified by silical gel chromatography using hexanes as eluant. The title compound was obtained as a yellow oil (0.189 g, 26% yield).

Provenance & Evidence