Pentadecane-1,15-diol (4.70 g, 19.2 mmol) was dissolved in cyclohexane (50 mL) and 48% HBr (2.4 mL, 21.2 mmol, 1.1 equiv) was added with vigorous stirring. The mixture was refluxed overnight. After cooling to room temperature, saturated sodium bicarbonate solution (100 mL) was added and the phases were separated. The aqueous phase was extracted with dichloromethane (3 x 50 mL). The combined organic layers were dried over MgSO 4 . After evaporation of the solvent, the product was purified by column chromatography (silica gel, 27 x 4 cm, cyclohexane/ethyl acetate, 4:1100% ethyl acetate) and separated as a white solid 15-bromo-1-pentadecanol. Yield: 3.39 g (58%).
