hydrogenchloride; copper; copper(l) chloride; calcium chloride in diethyl ether; Petroleum ether T=5°C; 1 h;

1: (i) Et2O, (ii) /BRN= 635680/ 2: aq. HCl, CaCl2 / CuCl, Cu View Scheme

1: Br2 / diethyl ether / 2 h / -10 °C 2: 70 percent / KOH / H2O; diethyl ether / 180 - 220 °C 3: 1.) MeI, Li / 1.) Et2O, 20 deg C, 1 h; 2.) 20 deg C, 12 h 4: 85 percent / CaCl2, CuCl, Cu, 12N HCl / diethyl ether; petroleum ether / 1 h / 5 °C View Scheme

1: 70 percent / KOH / H2O; diethyl ether / 180 - 220 °C 2: 1.) MeI, Li / 1.) Et2O, 20 deg C, 1 h; 2.) 20 deg C, 12 h 3: 85 percent / CaCl2, CuCl, Cu, 12N HCl / diethyl ether; petroleum ether / 1 h / 5 °C View Scheme

magnesium 1.) Et2O; 2.) 12 h, RT; 2 h, reflux; Yield given. Multistep reaction;