1: With sulfuric acid in acetonitrile T=0°C; Sandmeyer Reaction; 0.5 h; Inert atmosphere; 2: With sodium nitrite in water; acetonitrile T=0°C; Sandmeyer Reaction; 1 h; Inert atmosphere; 3: With potassium iodide in water; acetonitrile T=0 - 20°C; Sandmeyer Reaction; 1.08333 h; Inert atmosphere;

hydrogenchloride; potassium iodide; sodium nitrite in water

potassium carbonate in acetone T=40°C; 15 h;

potassium iodide in water T=0 - 20°C; 1.08333 h;

iodine; tert.-butyl lithium 1.) Et2O, pentane, -75 deg C, 30 min, 2.) Et2O, -75 deg C, 10 min; -20 deg C, 10 min; Yield given. Multistep reaction;

1: 98 percent / Et3N, CuI / Pd(PPh3)2Cl2 / toluene / 2 h / 20 °C 2: 99 percent / TBAF / tetrahydrofuran / 0.75 h / 20 °C View Scheme

lead(IV) acetate in acetic acid 24 h;