1: 2.) SOCl2 / 1.) CH2Cl2, RT, overnight, 2.) Et2O, RT, 1 h 2: 1.) 1.6N n-butyllithium, 2.) p-toluenesulfonylazide / 1.) ether, hexane, -40 deg C, 45 min, 2.) -40 deg C, 4 h 3: 79 percent / hexadecyl tributylphosphonium bromide, NaBH4 / toluene; H2O / 24 h / 80 °C 4: 52 percent / 48percent HBr / 18 h / Heating View Scheme

ammonium chloride; cadmium (II) chloride 1.) ether, from -5 deg C to reflux, 1 h, 2.) benzene, reflux, 1 h; Yield given. Multistep reaction;