1: 90 percent / NBS; PPh3 / benzene / 20 °C 2: 80 percent / acetonitrile / 6.5 h / 100 °C 3: 79 percent / AIBN; Bu3SnH / acetonitrile / 4 h / Heating View Scheme

1: NBS, Ph3P / benzene / 1.5 h / Heating 2: 1.) n-BuLi / 1.) THF, -100 deg C, 1 h 2.) -100 deg C, 2h and warm up to room temp. 3: 98 percent / 20percent aq. NaOH / methanol / 5 h / Heating 4: Diphenylphosphoroazidate, Et3N / benzene / 2 h / Heating 5: 24 h / Heating 6: 86 percent / Hydrogen, HCl / 5percent Pd/C / methanol 7: 48percent HBr / Heating View Scheme

1: NBS, Ph3P / benzene / 1.5 h / Heating 2: 1.) n-BuLi / 1.) THF, -100 deg C, 1 h 2.) -100 deg C, 2h and warm up to room temp. 3: 98 percent / 20percent aq. NaOH / methanol / 5 h / Heating 4: Diphenylphosphoroazidate, Et3N / benzene / 2 h / Heating 5: 24 h / Heating 6: 86 percent / Hydrogen, HCl / 5percent Pd/C / methanol View Scheme

N-bromosuccinmide; triphenylphosphine in benzene T=20°C; Substitution;

1: pyridine; phosphorus tribromide / dichloromethane / 1 h / 0 - 20 °C / |Inert atmosphere 2: ammonia / ethanol; water / 4 h / 20 °C View Scheme

1: NBS, Ph3P / benzene / 1.5 h / Heating 2: n-BuLi / tetrahydrofuran / temp. above -100 deg C View Scheme