hydrogen; nickel in acetone P=760 Torr; 24 h; Ambient temperature; Yield givenYields of byproduct given;

1: H2 / Raney Ni / acetone / 24 h / 760 Torr / Ambient temperature 2: Br2, pyridine / CH2Cl2 / 4 h / Ambient temperature View Scheme

1: H2 / Raney Ni / acetone / 24 h / 760 Torr / Ambient temperature 2: Br2, pyridine / CH2Cl2 / 4 h / Ambient temperature 3: 65 percent / polyphosphoric acid / 5.5 h / 105 °C 4: 93 percent / n-Buli / tetrahydrofuran; hexane / 1 h / -78 °C 5: 85 percent / BBr3 / CH2Cl2 / -78 - 20 °C View Scheme

1: H2 / Raney Ni / acetone / 24 h / 760 Torr / Ambient temperature 2: Br2, pyridine / CH2Cl2 / 4 h / Ambient temperature 3: 65 percent / polyphosphoric acid / 5.5 h / 105 °C 4: 93 percent / n-Buli / tetrahydrofuran; hexane / 1 h / -78 °C 5: 85 percent / BBr3 / CH2Cl2 / -78 - 20 °C View Scheme

1: H2 / Raney Ni / acetone / 24 h / 760 Torr / Ambient temperature 2: Br2, pyridine / CH2Cl2 / 4 h / Ambient temperature 3: 65 percent / polyphosphoric acid / 5.5 h / 105 °C 4: 93 percent / n-Buli / tetrahydrofuran; hexane / 1 h / -78 °C 5: 85 percent / BBr3 / CH2Cl2 / -78 - 20 °C View Scheme

sodium hydroxide in ethanol 2 h; Ambient temperature;