GERANYL BROMIDE

106-24-1

6138-90-5

General procedure for the synthesis of (E)-1-bromo-3,7-dimethylocta-2,6-diene from geraniol: Geraniol (10 g, 11.4 mL, 64.8 mmol, 1.0 eq.) was dissolved in dichloromethane (50 mL) under nitrogen protection. The solution was cooled to -20°C. A solution of phosphorus tribromide (3.0 mL, 32.4 mmol, 0.5 eq.) in dichloromethane (10 mL) was added slowly dropwise, keeping the reaction temperature below -16°C. The color of the solution changed to green/blue during the dropwise addition. The reaction mixture was stirred for 3 hours at about -20°C. Subsequently, water (50 mL) was carefully added at -40°C. The aqueous layer was extracted with ether (3 x 50 mL). The organic layers were combined and washed sequentially with saturated aqueous sodium bicarbonate (3 x 50 mL) and aqueous ammonium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a brown oily product (14.5 g, 66.6 mmol, quantitative yield).