1: With ethanol; sodium in toluene T=80°C; 2 h; 2: With hydrogenchloride; water in toluene pH=2 - 3; 3: With water in acetonitrile 2 h; Heating / reflux;

1: in ethanol; toluene T=80°C; 2 h; 2: With water in acetonitrile 2 h; Heating / reflux;

1.1: sodium ethanolate / toluene / 4 h / 80 °C 2.1: acetonitrile; water / 3 h / Reflux 3.1: bromine / tetrahydrofuran / 0.17 h / 20 °C 3.2: 2 h / 80 °C 4.1: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 2 h / 20 °C 5.1: caesium carbonate / palladium diacetate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene / acetonitrile / 16 h / 85 °C / Inert atmosphere View Scheme

triethylamine in dichloromethane T=0 - 20°C; 2 h; Inert atmosphere;

1.1: ammonia / ethanol / 16 h / -70 - 45 °C / 10343.2 Torr / Autoclave 1.2: 0.5 h / 0 °C / pH 2 / Inert atmosphere 2.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C View Scheme