hydrogenchloride in methanol 3 h; Heating;

1: 1.) t-BuNH2, Br2, 2.) 4-(dimethylamino)pyridine / 1.) toluene + CH2Cl2, from -78 to RT, 5 h, 2.) pyridine, room temp., 24 h 2: 94 percent / n-BuLi / tetrahydrofuran / 10 h / -78 - 20 °C 3: 65 percent / conc. HCl / methanol / 3 h / Heating View Scheme

1: 94 percent / n-BuLi / tetrahydrofuran / 10 h / -78 - 20 °C 2: 65 percent / conc. HCl / methanol / 3 h / Heating View Scheme

selenium T=350°C;

diethyl ether; bromine Erwaermen des Reaktionsprodukts mit N,N-Diaethyl-anilin;

Yield given. Multistep reaction;

1: 68 percent / N-bromosuccinimide / toluene; CH2Cl2 / 10 h / 1.) -78 deg C, 5 mni, 2.) RT, 10 h 2: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 3 h 3: 89 percent / n-BuLi / tetrahydrofuran; hexane / 7 h / -78 - 20 °C 4: 84 percent / NaI, trimethylsilyl chloride / acetonitrile / 3 h / Ambient temperature View Scheme