1: 1.) Zn(Cu) couple, 2.) Pd(PPh3)4 / 1.) DMF, benzene, room temp., 1 h, then 60 deg C, 4 h, 2.) DMF, benzene, room temp., 1 h 2: 80 percent / benzyltrimethylammonium tetrachloroiodate / acetic acid / 2.5 h / 70 °C 3: diethyl ether / 1.5 h / Ambient temperature View Scheme

1: 80 percent / benzyltrimethylammonium tetrachloroiodate / acetic acid / 2.5 h / 70 °C 2: diethyl ether / 1.5 h / Ambient temperature View Scheme

in diethyl ether 1.5 h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

in methanol 0.25 h; Heating; Title compound not separated from byproducts;