1H-imidazole; iodine; triphenylphosphine in dichloromethane 1.) r.t., 1 h, 2.) reflux, 1 h;

zinc in diethyl ether 12 h; Heating;

1: 76 percent / sodium / liquid ammonia 2: 88 percent / lithium aluminium hydride 3: 65 percent / H2SO4 conc, HBr-acetic acid / acetic acid; H2O / 8 h, rt; 8 h reflux 4: Zn activated / diethyl ether / 12 h / Heating View Scheme

1: 88 percent / lithium aluminium hydride 2: 65 percent / H2SO4 conc, HBr-acetic acid / acetic acid; H2O / 8 h, rt; 8 h reflux 3: Zn activated / diethyl ether / 12 h / Heating View Scheme

Wilkinson's catalyst T=205°C;

Yield given. Multistep reaction;