Diethyl Ether → Farnesyl bromide

Participants

Reaction Steps

Following the procedure reported by G. Pala et al. in Helv. Chim. Acta., 53, 1827- 1832 (1970), a mixture of 666 g of nerolidol (cis:trans= 40:60 ), 2,000 ml of diethyl ether and 20 ml of pyridine was cooled at -5° - -10° C. Thereto, 300 g of phosphorus tribromide was added dropwise slowly at the same temperature. Thereafter, the reaction was completed by further stirring of the mixture for 12 hours at the same temperature. The reaction mixture was poured into water and neutralized with sodium bicarbonate. The ether layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off in vacuo at room temperature to give 760 g of farnesyl bromide which showed orange color and irritating odor. As this substance was relatively unstable, it was brought to the following reaction without further purification or kept in a cold place.

Provenance & Evidence