1: 79.2 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C 2: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C 3: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C 4: 1.) H2, quinoline, 2.) H2O / 1.) Lindlar's cat. / 1.) AcOEt View Scheme

carbon tetrabromide; triphenylphosphine in dichloromethane T=0°C; 0.666667 h;

1: 79.2 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C 2: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C 3: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C View Scheme

1: PBr3, Py / diethyl ether / Heating 2: CuCl / tetrahydrofuran 3: H2, quinoline / Lindlar catalyst / ethanol View Scheme

1: With dimethylsulfide borane complex; cyclohexene 2: With acetic acid 3: With sodium hydroxide; dihydrogen peroxide