carbon tetrabromide; triphenylphosphine in dichloromethane T=0°C; 2 h;

1: 1.) BuLi / 1.) THF, hexane, from -80 deg C to RT, 2.) THF, hexane, RT, 4 h 2: 100 percent / 0.1N HCl / methanol / 6 h 3: 67 percent / CBr4, PPh3 / CH2Cl2 / 2 h / 0 °C View Scheme

1: 100 percent / 0.1N HCl / methanol / 6 h 2: 67 percent / CBr4, PPh3 / CH2Cl2 / 2 h / 0 °C View Scheme

sodium tetrahydroborate in methanol 1 h; Ambient temperature;