lithium aluminium tetrahydride in diethyl ether 1.) ice-cooling 2.) reflux, 3 h;

1: 100 percent / H2 / Pd/C / methanol / 4 h / 20 °C / 760 Torr 2: 100 percent / aq. NaOH; citrimide / tetrahydrofuran / 5 h / Heating 3: SOCl2 / 2 h / Heating 4: 19.30 g / NH3 / methanol / -5 °C 5: 65 percent / aq. NaOH; Br2 / 2 h / 70 °C View Scheme