triphenylphosphine in benzene T=20°C; 24 h; Title compound not separated from byproducts;

1.1: MeLi; iPr2NH / diethyl ether / -78 °C 1.2: 69 percent / diethyl ether / 0.5 h / -90 °C 2.1: 79 percent / bromine / pentane / 0.5 h / -78 °C 3.1: 100 percent / NaN3 / acetic acid; ethanol; H2O / 20 h / 0 °C 4.1: PPh3 / benzene / 24 h / 20 °C View Scheme

1: 100 percent / NaN3 / ethanol; H2O; acetic acid / 20 h / 0 °C 2: PPh3 / benzene / 24 h / 20 °C View Scheme

1: 79 percent / bromine / pentane / 0.5 h / -78 °C 2: 100 percent / NaN3 / acetic acid; ethanol; H2O / 20 h / 0 °C 3: PPh3 / benzene / 24 h / 20 °C View Scheme

1: 83 percent / bromine / pentane / 0.5 h / -78 °C 2: 100 percent / NaN3 / ethanol; H2O; acetic acid / 20 h / 0 °C 3: PPh3 / benzene / 24 h / 20 °C View Scheme

1.1: MeLi; iPr2NH / diethyl ether / -78 °C 1.2: 58 percent / diethyl ether / 0.5 h / -90 °C 2.1: 83 percent / bromine / pentane / 0.5 h / -78 °C 3.1: 100 percent / NaN3 / ethanol; H2O; acetic acid / 20 h / 0 °C 4.1: PPh3 / benzene / 24 h / 20 °C View Scheme

1: 100 percent / NaN3 / acetic acid; ethanol; H2O / 20 h / 0 °C 2: PPh3 / benzene / 24 h / 20 °C View Scheme