phosphorus; bromine T=85 - 90°C;

1: 12.3 g / LiAlD4 / tetrahydrofuran / 2 h / Heating 2: 10.0 g / phosphorus tribromide / 2 h / Heating View Scheme

1.1: NaOH / methanol / pH 8.0 1.2: 15.7 g / NaOH; D2O / Pt/C / 110 h / 220 °C 2.1: 12.3 g / LiAlD4 / tetrahydrofuran / 2 h / Heating 3.1: 10.0 g / phosphorus tribromide / 2 h / Heating View Scheme

phosphorus tribromide 2 h; Heating;

sodium in diethyl ether 24 h; Ambient temperature;

1: 1.) EtONa / 1.) EtOH, 50 deg C, 1 h, 2.) EtOH, 30 deg C, 6 h 2: 1.) D2O, NaOD, 2.) D2SO4 / 1.) reflux, 6 h, 2.) reflux, 4.5 h 3: 90.8 percent / LiAlD4 / diethyl ether / 8 h / Heating 4: 85.1 percent / red phosphorous, Br2 / 85 - 90 °C View Scheme