hydrogen bromide in acetic acid 3 h; Heating;

1: 58 percent / conc. H2SO4 / H2O / 100 °C 2: 95 percent / SOCl2 / 1 h / Ambient temperature 3: 62 percent / hydrogen / Raney-Ni / tetrahydrofuran / 40 - 50 °C 4: bromocyanogene / tetrahydrofuran / 1 h / Heating 5: dimethylformamide / 2 h / Heating 6: 81 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 7: 93 percent / 66 percent HBr / acetic acid / 3 h / Heating View Scheme

1: 62 percent / hydrogen / Raney-Ni / tetrahydrofuran / 40 - 50 °C 2: bromocyanogene / tetrahydrofuran / 1 h / Heating 3: dimethylformamide / 2 h / Heating 4: 81 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 5: 93 percent / 66 percent HBr / acetic acid / 3 h / Heating View Scheme

1: 95 percent / SOCl2 / 1 h / Ambient temperature 2: 62 percent / hydrogen / Raney-Ni / tetrahydrofuran / 40 - 50 °C 3: bromocyanogene / tetrahydrofuran / 1 h / Heating 4: dimethylformamide / 2 h / Heating 5: 81 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 6: 93 percent / 66 percent HBr / acetic acid / 3 h / Heating View Scheme

1: 89 percent / 40 percent Triton B / tetrahydrofuran; methanol / 1 h / Ambient temperature 2: 58 percent / conc. H2SO4 / H2O / 100 °C 3: 95 percent / SOCl2 / 1 h / Ambient temperature 4: 62 percent / hydrogen / Raney-Ni / tetrahydrofuran / 40 - 50 °C 5: bromocyanogene / tetrahydrofuran / 1 h / Heating 6: dimethylformamide / 2 h / Heating 7: 81 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 8: 93 percent / 66 percent HBr / acetic acid / 3 h / Heating View Scheme

1: bromocyanogene / tetrahydrofuran / 1 h / Heating 2: dimethylformamide / 2 h / Heating 3: 81 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 4: 93 percent / 66 percent HBr / acetic acid / 3 h / Heating View Scheme

1: 81 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 2: 93 percent / 66 percent HBr / acetic acid / 3 h / Heating View Scheme