General procedure for the synthesis of 2-cyclohexylethane bromoethane from 2-cyclohexylethanol: In a 1-liter round-bottomed flask fitted with a reflux condenser, 88.7 g (0.693 mol) of 2-cyclohexylethanol was added, followed by the slow addition of 164 g of concentrated sulfuric acid and 200 g of hydrobromic acid (48% aqueous), cooled in an ice bath. The reaction mixture was heated to reflux for 6 hours. After completion of the reaction, it was cooled to room temperature and the reaction was quenched by the addition of 400 g of ice. The aqueous phase was extracted with 400 ml of pentane and the organic layers were combined. The organic layer was washed sequentially with 2M NaOH solution and water and then dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure and the product was finally purified by vacuum distillation to give 112.7 g (85% yield) of 2-cyclohexylethyl bromide as a colorless oil.1H-NMR (400 MHz, CDCl3): δ= 3.40 (2H, t, CH2Br), 1.73-1.61 (m, 7H), 1.44 (m, 1H), 1.26-1.11 ( m, 3H), 0.92-0.84 (m, 2H) ppm.
