Carbon tetrabromide → 2-[2-[2-Bromoethylthio]ethyl]-1,3-dioxolane

Participants

Reaction Steps

To a stirred cooled (<0°) solution of 2-[2-[1,3-dioxolan-2-yl]ethylthio]ethanol (13.6 g, prepared by the condensation between mercaptoethanol and 2-[2-bromoethyl]-1,3-dioxolane employing sodium hydride) in dry acetonitrile (150 ml) was added triphenylphosphine (20 g) and carbon tetrabromide (38 g). The solution was stirred for 4 hours. The solvent was removed under reduced pressure and the residue pre-absorbed onto silica. The material was flash chromatographed over silica using 10% ethylacetate/petroleum ether as eluant to afford the subtitled compound as a clear oil (4.45 g). The material was used in the next step without further purification.

Provenance & Evidence