thionyl chloride 2 h; Heating;

1: pyridine / CH2Cl2 / 2 h / Ambient temperature 2: N-bromosuccinimide, benzoyl peroxide / CCl4 / 1 h / Heating 3: DBU / benzene / 2 h / Ambient temperature 4: 84 percent / tetrahydrofuran / 2 h / 0 °C 5: 88 percent / NaIO4, H2O / methanol / Ambient temperature 6: 23 percent / 1 h / Heating View Scheme

ammonia in diethyl ether T=-10°C;

diethyl ether

1: 71 percent / Et3N / toluene / 3 h / Ambient temperature 2: 28 percent / 750 °C / 0.1 - 1 Torr View Scheme

1: 18 h / Reflux 2: 2,2'-azo-bisisobutyronitrile; N-bromosuccinmide / tetrachloromethane / 3 h / 70 °C / Inert atmosphere; Reflux 3: ammonia / methanol / 14 h / 20 °C / Inert atmosphere View Scheme

1: 18 h / Reflux 2: 2,2'-azo-bisisobutyronitrile; N-bromosuccinmide / tetrachloromethane / 3 h / 70 °C / Inert atmosphere; Reflux 3: ammonia / methanol / 14 h / 20 °C / Inert atmosphere 4: bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]octane / tetrahydrofuran / 14 h / 60 °C / Inert atmosphere View Scheme

triethylamine in diethyl ether T=20°C; 1 h; Yield given;