Synthesis

Alkyl alcohols (5.0 mmol, 1 equiv) were dissolved in dry 5 ml of dichloromethane in a dry 25 ml flask. It was then cooled to 0 C and the dissolved material was added to a solution of CBr4 (2.5 g, 7.5 mmol, 1.5 equiv.) in DCM (10 mL) under Ar atmosphere. PPh3 (2.0 g, 7.5 mmol, 1.5 equiv) was then dissolved in dry dichloromethane (5 ml). The resulting dissolved material was slowly added to the above reaction mixture. The resulting reaction mixture was slowly brought to room temperature and stirred for 4 hours. Upon completion of the reaction, the reaction mixture was concentrated directly under reduced pressure to remove the reaction solvent. The resulting residue was purified by silica gel column chromatography (n-hexane) to afford the target product molecule 1-bromo-8-phenyloctane.