1: With sodium hydroxide; copper; copper(II) sulfate in water 30 h; Heating / reflux; 2: With sodium sulfide in water T=20°C; 3: With hydrogenchloride; hydrogen sulfide more than 3 stages;

sulfuric acid Diazotization;

1: aqueous alkaline solution 2: aqueous H2SO4 / Diazotization View Scheme

sulfuric acid T=70°C; 18 h; Sealed tubeHeating / reflux;

sulfuric acid; nitric acid T=55 - 60°C; 96 h;

thionyl chloride T=0°C; 24 h; Heating / reflux;

borane-THF in tetrahydrofuran T=20°C; Cooling with ice;

T=95°C; 16 h; Inert atmosphere;

1: borane-THF / tetrahydrofuran / 20 °C / Cooling with ice 2: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C 3: triethylamine / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 100 °C / 15001.5 Torr / Inert atmosphere; autoclave vessel 4: toluene-4-sulfonic acid / methanol / 2 h / 20 °C View Scheme

1: borane-THF / tetrahydrofuran / 20 °C / Cooling with ice 2: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C 3: triethylamine / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 100 °C / 15001.5 Torr / Inert atmosphere; autoclave vessel 4: toluene-4-sulfonic acid / methanol / 2 h / 20 °C 5: manganese(IV) oxide / chloroform / 7 h / Reflux View Scheme