pyridine; phosphorus tribromide in diethyl ether 1) 16 h, rt, 2) 1 h, reflux;

1: 1.) LiN2 / 1.) liq. ammonia, 1 h, 2.) liq. ammonia, THF, 12 h 2: pyridine / CH2Cl2 3: LiBr / acetone / 1 h / Heating View Scheme

1: 1.) EtMgBr, 2.) CuCl / 1.) THF, 20 deg C, 2 h, 2.) THF, 20 deg C, 24 h 2: 1.2 N HCl / methanol / 1 h View Scheme

1: 1.) EtMgBr, 2.) CuCl / 1.) THF, 20 deg C, 2 h, 2.) THF, 20 deg C, 24 h 2: 1.2 N HCl / methanol / 1 h 3: H2, quinoline / Lindlar catalyst / ethanol 4: MnO2 / CH2Cl2 / 24 h / 20 °C 5: 1.) BuLi / 1.) THF, hexane, 2.) THF, hexane, 20 deg C, 4 h View Scheme

1: 75 percent / CuCl 2: 82 percent / H2 / Lindlar catalyst 3: 43 percent / PPh3Br2 View Scheme