a Farnesol → Farnesyl bromide

Participants

Reaction Conditions

Reaction Steps

Into an argon-replaced 1 liter reaction vessel, 66.6 g (0.3 mol) of farnesol (all trans-form) was charged, and 300 ml of isopropyl ether was further added to dissolve farnesol. The resulting solution was cooled to -20° C., and thereafter 32.5 g (0.12 mol) of phosphorus tribromide was added to carry out reaction at -20° C. to -10° C. for 2 hours. The reaction mixture thus obtained was poured into 400 ml of an aqueous 5% sodium carbonate solution, and the liquid was separated. The organic layer was washed with saturated brine, followed by distillation of the solvent to obtain 77.0 g of farnesyl bromide (yield: 90%). Data of physical properties of this compound are shown below.

Provenance & Evidence