hydrogen bromide T=145 - 150°C; 5 h;

1: pyridine, piperidine 2: conc. H2SO4 3: H2 / 5percent Pd/C / ethanol / 45 °C 4: sodium wire / diethyl ether / 18 h / Ambient temperature 5: ethanol / 7 h / Heating 6: 69 percent / NaOH / H2O; ethanol / 60 °C 7: 45 percent / 2.) 2 N HBr / 5 h / 145 - 150 °C View Scheme

1: conc. H2SO4 2: H2 / 5percent Pd/C / ethanol / 45 °C 3: sodium wire / diethyl ether / 18 h / Ambient temperature 4: ethanol / 7 h / Heating 5: 69 percent / NaOH / H2O; ethanol / 60 °C 6: 45 percent / 2.) 2 N HBr / 5 h / 145 - 150 °C View Scheme

1: H2 / 5percent Pd/C / ethanol / 45 °C 2: sodium wire / diethyl ether / 18 h / Ambient temperature 3: ethanol / 7 h / Heating 4: 69 percent / NaOH / H2O; ethanol / 60 °C 5: 45 percent / 2.) 2 N HBr / 5 h / 145 - 150 °C View Scheme

1: sodium wire / diethyl ether / 18 h / Ambient temperature 2: ethanol / 7 h / Heating 3: 69 percent / NaOH / H2O; ethanol / 60 °C 4: 45 percent / 2.) 2 N HBr / 5 h / 145 - 150 °C View Scheme

1: 69 percent / NaOH / H2O; ethanol / 60 °C 2: 45 percent / 2.) 2 N HBr / 5 h / 145 - 150 °C View Scheme