1: 90 percent / CuI / 1 h / -78 °C 2: 94 percent / 2 N KOH / H2O / 1 h / Heating 3: thiophenol, 2,2'-azobis(isobutyronitrile) / 2 h / 80 °C 4: SOCl2 View Scheme

copper(l) iodide in tetrahydrofuran T=-78°C; 1 h;