Bromine → 1-Bromo-3-ethyladamantane

1-Bromo-3-ethyladamantane was prepared from 1-ethyladamantane (K. Gerzon et al, J. Med. Chem., 6, 760, 1963) by stirring 0.944 grams (5.76 mmol) of 1-ethyladamantane with 10 ml of liquid bromine for 4 hours, over which time the temperature was increased to reflux. The heat was removed and after cooling, a 40 ml portion of carbon tetrachloride was added. The mixture was poured into 120 ml of ice water and enough solid sodium sulfite was added with stirring to destroy the excess bromine. The layers were separated and the aqueous phase was extracted with three portions of carbon tetrachloride. The combined extracts were washed with water, then 5% aqueous sodium bicarbonate solution, then dried over magnesium sulfate (anhydrous). Evaporation of solvent yielded a yellow liquid which was distilled to afford 1.263 grams (90.3%) of 1-bromo-3-ethyladamantane, bp 114°-115° C. (3.5 mm).