bromine in dichloromethane T=0°C;

1: 1.) sodium; / 1.) toluene, 0 deg C, 2 h; 2.) reflux, 16 h 2: 94 percent / bromine / CH2Cl2 / 0 °C View Scheme

1: 83 percent / phosphorus oxychloride / 3 h / Heating 2: 1.) sodium; / 1.) toluene, 0 deg C, 2 h; 2.) reflux, 16 h 3: 94 percent / bromine / CH2Cl2 / 0 °C View Scheme