1: acetic acid; sulfuric acid; aqueous sodium nitrite solution; aqueous potassium iodide solution 2: copper-powder / 300 °C 3: tin; aq.-ethanolic HCl View Scheme

(i) aq. NaNO2, aq. HBr, (ii) CuBr, aq. HBr; Multistep reaction;

hydrogenchloride; sodium nitrite in water; sodium hydrogencarbonate; acetic acid

1: 2-Amino-5-nitrotrifluoromethylbenzene With sulfuric acid in water 2: With sodium nitrite in water T=0°C; 0.333333 h; 3: potassium cyanide With sodium carbonate; copper(II) sulfate more than 3 stages;

N-chloro-succinimide in acetonitrile T=150°C; 0.25 h; Microwave irradiation;

1: With hydrogen bromide T=20 - 70°C; 0.166667 h; 2: With dihydrogen peroxide in water T=60 - 70°C; 3 h;

1: acetic acid; sulfuric acid; aqueous sodium nitrite solution; aqueous potassium iodide solution 2: H2SO4 View Scheme

1.1: sulfuric acid; sodium nitrite / 1 h 1.2: 65 h / 100 °C / Cooling with ice 1.3: 20 °C 2.1: water; ammonium chloride; zinc / methanol / 1 h View Scheme

1: With sulfuric acid; sodium nitrite 1 h; 2: With water T=100°C; 65 h; Cooling with ice; 3: With ammonia in water T=20°C;

1: 81 percent / Br2 / acetic acid / 1.) 45 deg C, 2.5 h, 2.) reflux, 4.75 h 2: 56 percent / ZnCl2 / benzene / 32 h / Heating 3: 86 percent / SnCl2*2H2O / ethanol / 1.) reflux, 0.5 h, 2.) room temp., 13 h 4: 1.) NaNO2, 48percent HBF4, 2.) 50percent aq. H3PO2 / 1.) H2O, 0 deg C, 2.5 h, 2.) CHCl3, 24 h, room temp. 5: 69 percent / conc. HCl / ethanol / 75 h / Heating 6: 1.) conc. HCl, NaNO2, 2.) KI / 1.) H2O, 0-5 deg C, 2.) room temp., 22 h 7: 58 percent / powdered Mg / tetrahydrofuran / 1 h / Heating View Scheme