n-butyllithium in tetrahydrofuran; hexane

1: PCl5, POCl3 / 8 h / Heating 2: 3 h / Heating 3: K3<Fe(CN)6>, conc. NaOH / 3 h / 5 °C 4: PCl5, POCl3 / 8 h / Heating 5: NH3 (gas), phenol, acetamide / 8 h / 160 °C View Scheme

1.1: phosphorus pentabromide; phosphorus oxytribromide / 20 - 80 °C / Inert atmosphere 1.2: Alkaline conditions 2.1: 120 °C / Inert atmosphere; cooling with ice 3.1: potassium hexacyanoferrate(III); sodium hydroxide / water / 4 - 20 °C View Scheme

1.1: phosphorus pentabromide; phosphorus oxytribromide / 20 - 80 °C / Inert atmosphere 1.2: Alkaline conditions 2.1: 120 °C / Inert atmosphere; cooling with ice 3.1: potassium hexacyanoferrate(III); sodium hydroxide / water / 4 - 20 °C 4.1: phosphorus pentabromide; phosphorus oxytribromide / 75 °C / Inert atmosphere; cooling with ice 4.2: Alkaline conditions View Scheme