hydrogenchloride; sodium methylate 1.) benzene, 0 deg C to room temp., then room temp., 1.5 h, 2.) water, 100 deg C, 3 h, then room temp., overnight; Yield given. Multistep reaction;

1: 99 percent / K2CO3 / methanol / 0.03 h / Ambient temperature 2: 46 percent / NBS / AIBN / CHCl3; CCl4 / 15 h / 65 °C View Scheme

nitric acid; sodium nitrite

1: 99 percent / K2CO3 / methanol / 0.03 h / Ambient temperature 2: 46 percent / NBS / AIBN / CHCl3; CCl4 / 15 h / 65 °C 3: 93 percent / W-2 Raney Nickel / tetrahydrofuran / 1.) 0 deg C to room temp., 2.) room temp., 30 min 4: 85 percent / NBS / CCl4 / 120 h View Scheme

sodium hydroxide T=20°C; 3 h;