1.1: hydrogenchloride / acetonitrile; water / 0.25 h / -10 - 20 °C 1.2: 0.5 h 1.3: 0.5 h / -10 - 20 °C 2.1: Ba(OH)2*8H2O / ethanol / 20 °C 3.1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 100 °C / |Inert atmosphere 4.1: boron trifluoride diethyl etherate / acetonitrile / 4 h / 45 °C View Scheme

1: 4'-amino-3'-bromoacetophenone With sulfuric acid in acetic acid T=0°C; 0.166667 h; 2: With sodium nitrite in water; acetic acid 0.5 h; 3: copper (I) cyanide; potassium cyanide in water; acetic acid T=0 - 20°C; 2.5 h;

hydrogenchloride; sodium nitrite 1.) H2O, 5 deg C; 2.) 40-50 deg C, 0.5 h; Yield given. Multistep reaction. Yields of byproduct given;

1: 1.) NaNO2, conc. HCl / 1.) H2O, 5 deg C; 2.) 0.5 h 2: 93.4 percent / conc. H2SO4 / H2O; acetic acid / 5 h / Heating 3: 65.5 percent / K2CO3, Cu / 2 h / 157 - 170 °C 4: 95.1 percent / conc. H2SO4 / 4.5 h / Heating 5: 1.) sulfur, morpholine; 2.) KOH / 1.) reflux, 17 h; 2:) H2O, 95percent EtOH, reflux, 16 h View Scheme

1: 58 percent / FeCl3 / dimethylformamide / Heating 2: 74 percent / CuBr2 / tetrahydrofuran / Heating 3: ethanol 4: NaBH4 View Scheme