hydrogen bromide T=130 - 140°C; 5 h;

1: 70 percent / thionyl chloride / benzene / 24 h / Heating 2: 1.) NaH / 1.) EtOH, 10 min, 2.) EtOH, reflux, 24 h 3: 93 percent / 48percent HBr / 5 h / 130 - 140 °C View Scheme

1: 1.) NaH / 1.) EtOH, 10 min, 2.) EtOH, reflux, 24 h 2: 93 percent / 48percent HBr / 5 h / 130 - 140 °C View Scheme

1: 67 percent / BH3 / tetrahydrofuran / 16 h / Heating 2: 70 percent / thionyl chloride / benzene / 24 h / Heating 3: 1.) NaH / 1.) EtOH, 10 min, 2.) EtOH, reflux, 24 h 4: 93 percent / 48percent HBr / 5 h / 130 - 140 °C View Scheme

1: 61 percent / KOH / 96 h / Heating 2: 67 percent / BH3 / tetrahydrofuran / 16 h / Heating 3: 70 percent / thionyl chloride / benzene / 24 h / Heating 4: 1.) NaH / 1.) EtOH, 10 min, 2.) EtOH, reflux, 24 h 5: 93 percent / 48percent HBr / 5 h / 130 - 140 °C View Scheme

1: 90 percent / aq. KOH / ethanol / 4 h / Ambient temperature 2: 61 percent / KOH / 96 h / Heating 3: 67 percent / BH3 / tetrahydrofuran / 16 h / Heating 4: 70 percent / thionyl chloride / benzene / 24 h / Heating 5: 1.) NaH / 1.) EtOH, 10 min, 2.) EtOH, reflux, 24 h 6: 93 percent / 48percent HBr / 5 h / 130 - 140 °C View Scheme

1: 75 percent / LiAlH4 / diethyl ether / 6 h / Ambient temperature 2: 80 percent / thionyl chloride / 0.42 h / Heating 3: 45 percent / sodium ethoxide / ethanol / 4.5 h / Heating 4: 80 percent / HBr / H2O / 0.33 h / Heating View Scheme