hydrogen bromide in acetic acid T=130°C; 1.5 h;

1: 1.) NaH, HMPA / 1.) RT, 2.) 25 deg C, 1 h 2: tetrakis(triphenylphosphine)palladium / tetrahydrofuran / 1.5 h / Heating 3: 1.) KMnO4, 2.) HCl gas / 1.) H2O, 1 h, 2.) overnight 4: H2, conc. HCl / PtO2 / methanol / 6 h / 2585.7 Torr 5: triethylamine / CCl4 / 3 h / 0 - 20 °C 6: LiAlH4 / tetrahydrofuran / 18 h / Ambient temperature 7: triethylamine / tetrahydrofuran / 0.08 h 8: triethylamine / tetrahydrofuran; ethanol; H2O / 1 h / 55 °C 9: 195 mg / HBr gas / acetic acid / 1.5 h / 130 °C View Scheme

1: tetrakis(triphenylphosphine)palladium / tetrahydrofuran / 1.5 h / Heating 2: 1.) KMnO4, 2.) HCl gas / 1.) H2O, 1 h, 2.) overnight 3: H2, conc. HCl / PtO2 / methanol / 6 h / 2585.7 Torr 4: triethylamine / CCl4 / 3 h / 0 - 20 °C 5: LiAlH4 / tetrahydrofuran / 18 h / Ambient temperature 6: triethylamine / tetrahydrofuran / 0.08 h 7: triethylamine / tetrahydrofuran; ethanol; H2O / 1 h / 55 °C 8: 195 mg / HBr gas / acetic acid / 1.5 h / 130 °C View Scheme

1: 1.) Br2, 2.) NaBH4 / 1.) reflux, 18 h, 2.) EtOH, from -10 to 0 deg C 2: 1.) NaH, HMPA / 1.) RT, 2.) 25 deg C, 1 h 3: tetrakis(triphenylphosphine)palladium / tetrahydrofuran / 1.5 h / Heating 4: 1.) KMnO4, 2.) HCl gas / 1.) H2O, 1 h, 2.) overnight 5: H2, conc. HCl / PtO2 / methanol / 6 h / 2585.7 Torr 6: triethylamine / CCl4 / 3 h / 0 - 20 °C 7: LiAlH4 / tetrahydrofuran / 18 h / Ambient temperature 8: triethylamine / tetrahydrofuran / 0.08 h 9: triethylamine / tetrahydrofuran; ethanol; H2O / 1 h / 55 °C 10: 195 mg / HBr gas / acetic acid / 1.5 h / 130 °C View Scheme

1: tetrakis(triphenylphosphine)palladium / tetrahydrofuran / 1.5 h / Heating 2: 1.) KMnO4, 2.) HCl gas / 1.) H2O, 1 h, 2.) overnight 3: H2, conc. HCl / PtO2 / methanol / 6 h / 2585.7 Torr 4: triethylamine / CCl4 / 3 h / 0 - 20 °C 5: LiAlH4 / tetrahydrofuran / 18 h / Ambient temperature 6: triethylamine / tetrahydrofuran / 0.08 h 7: triethylamine / tetrahydrofuran; ethanol; H2O / 1 h / 55 °C 8: 195 mg / HBr gas / acetic acid / 1.5 h / 130 °C View Scheme

1: H2, conc. HCl / PtO2 / methanol / 6 h / 2585.7 Torr 2: triethylamine / CCl4 / 3 h / 0 - 20 °C 3: LiAlH4 / tetrahydrofuran / 18 h / Ambient temperature 4: triethylamine / tetrahydrofuran / 0.08 h 5: triethylamine / tetrahydrofuran; ethanol; H2O / 1 h / 55 °C 6: 195 mg / HBr gas / acetic acid / 1.5 h / 130 °C View Scheme

1: 1.) KMnO4, 2.) HCl gas / 1.) H2O, 1 h, 2.) overnight 2: H2, conc. HCl / PtO2 / methanol / 6 h / 2585.7 Torr 3: triethylamine / CCl4 / 3 h / 0 - 20 °C 4: LiAlH4 / tetrahydrofuran / 18 h / Ambient temperature 5: triethylamine / tetrahydrofuran / 0.08 h 6: triethylamine / tetrahydrofuran; ethanol; H2O / 1 h / 55 °C 7: 195 mg / HBr gas / acetic acid / 1.5 h / 130 °C View Scheme

1: triethylamine / tetrahydrofuran / 0.08 h 2: triethylamine / tetrahydrofuran; ethanol; H2O / 1 h / 55 °C 3: 195 mg / HBr gas / acetic acid / 1.5 h / 130 °C View Scheme

1: triethylamine / CCl4 / 3 h / 0 - 20 °C 2: LiAlH4 / tetrahydrofuran / 18 h / Ambient temperature 3: triethylamine / tetrahydrofuran / 0.08 h 4: triethylamine / tetrahydrofuran; ethanol; H2O / 1 h / 55 °C 5: 195 mg / HBr gas / acetic acid / 1.5 h / 130 °C View Scheme

1: triethylamine / tetrahydrofuran; ethanol; H2O / 1 h / 55 °C 2: 195 mg / HBr gas / acetic acid / 1.5 h / 130 °C View Scheme