N-bromosuccinmide; dimethylsulfide in dichloromethane T=0°C; 3 h;

N-bromosuccinmide; lithium aluminium tetrahydride 1.) THF, 0 deg C, 2.) CH2Cl2, Me2S, -20 deg C, 3.) 0 deg C, 3h; Yield given. Multistep reaction;

1: NBS, benzoyl peroxide / CCl4 / 0.5 h / Irradiation 2: CCl4; dimethylformamide / 1 h / Ambient temperature 3: LiAlH4 / tetrahydrofuran / 1 h / 0 °C 4: 86 percent / Me2S, NBS / CH2Cl2 / 3 h / 0 °C View Scheme

1: CCl4; dimethylformamide / 1 h / Ambient temperature 2: LiAlH4 / tetrahydrofuran / 1 h / 0 °C 3: 86 percent / Me2S, NBS / CH2Cl2 / 3 h / 0 °C View Scheme

1: 1.) NBS / 1.) CCl4, irradiation, reflux 30 min, 2.) DMF, room temperature, 1 h 2: 1.) LiAlH4, 2.) NBS / 1.) THF, 0 deg C, 2.) CH2Cl2, Me2S, -20 deg C, 3.) 0 deg C, 3h View Scheme