Yield given. Multistep reaction;

bromine; triphenylphosphine in tetrachloromethane 0.5 h; Ambient temperature;

1: pyridine 2: 1) LiCuCl4; 2) Mg; 3) diisobutylaluminium hydride / 1) abs. THF, -45 deg C; 2) diethyl ether, -45 deg C, 3 h; 3) diethyl ether, toluene, -10 deg C. 3: 81 percent / triphenylphosphine, bromine / CCl4 / 0.5 h / Ambient temperature View Scheme

1: 1) LiCuCl4; 2) Mg; 3) diisobutylaluminium hydride / 1) abs. THF, -45 deg C; 2) diethyl ether, -45 deg C, 3 h; 3) diethyl ether, toluene, -10 deg C. 2: 81 percent / triphenylphosphine, bromine / CCl4 / 0.5 h / Ambient temperature View Scheme

1: 1) coprous iodide, 2,2'-bipyridyl; 2) Mg / 1) abs. THF, 10 min; 2) abs. THF 2: 1) water, p-toluenesulfonic acid; 2) pyridine / 1) methanol, room temp., 2) room temp. View Scheme

Yield given. Multistep reaction;