hydrogen; platinum(IV) oxide in ethanol P=760 Torr;

1: 44 percent / bromine, aq. NaOH / 1.) 0 deg C, 0.5 h, 2.) RT, 2 h 2: 79 percent / potassium carbonate / dimethylsulfoxide / 1 h / Heating 3: 45 percent / nitric acid, conc. sulfuric acid / 2 h / 60 - 65 °C 4: 44 percent / H2 / platinum oxide / ethanol / 760 Torr View Scheme

1: 79 percent / potassium carbonate / dimethylsulfoxide / 1 h / Heating 2: 45 percent / nitric acid, conc. sulfuric acid / 2 h / 60 - 65 °C 3: 44 percent / H2 / platinum oxide / ethanol / 760 Torr View Scheme

1: 45 percent / nitric acid, conc. sulfuric acid / 2 h / 60 - 65 °C 2: 44 percent / H2 / platinum oxide / ethanol / 760 Torr View Scheme