1: triethylamine / CH2Cl2 / -78 °C 2: 4 percent / methanol / Heating View Scheme

1: 83 percent / aluminium chloride / benzene / 0.5 h / Heating 2: 18 percent / nitric acid, acetic acid / 4 h / 15 - 16 °C / further nitration agents 3: potassium carbonate / dimethylformamide / 14 h / Ambient temperature 4: 1.) hydrogen / 1.) palladized charcoal / 1.) ethanol, 18 h View Scheme

1: 18 percent / nitric acid, acetic acid / 4 h / 15 - 16 °C / further nitration agents 2: potassium carbonate / dimethylformamide / 14 h / Ambient temperature 3: 1.) hydrogen / 1.) palladized charcoal / 1.) ethanol, 18 h View Scheme

1: 77 percent / bromine, aluminium powder 2: 83 percent / aluminium chloride / benzene / 0.5 h / Heating 3: 18 percent / nitric acid, acetic acid / 4 h / 15 - 16 °C / further nitration agents 4: potassium carbonate / dimethylformamide / 14 h / Ambient temperature 5: 1.) hydrogen / 1.) palladized charcoal / 1.) ethanol, 18 h View Scheme

in methanol Heating;

1: potassium carbonate / dimethylformamide / 14 h / Ambient temperature 2: 1.) hydrogen / 1.) palladized charcoal / 1.) ethanol, 18 h View Scheme

hydrogen; palladium on activated charcoal 1.) ethanol, 18 h; Multistep reaction;

1: 26 percent / copper(II) nitrate trihydrate, acetic anhydride / 1.5 h / 30 °C 2: 1.) hydrogen / 1.) palladized charcoal / 1.) ethanol, 18 h View Scheme