nitric acid T=0°C;

nitric acid; acetic acid in water T=20°C; 1 h; regioselective reaction;

1: Br2, acetic acid 2: 92 percent / concd. HNO3 / 0 °C View Scheme

1: 80.7 percent / MeONa / dimethylsulfoxide / 0.5 h / 130 °C 2: NaBH4, NiCl2 x 6 H20 / benzene; methanol / 0.5 h / Ambient temperature 3: pyridine / 1 h / Ambient temperature 4: 85.2 percent / anh. K2CO3, Cu, CuBr / nitrobenzene / 5 h / Heating 5: LiAlH4 / diethyl ether / 0.5 h / 0 - 5 °C View Scheme

potassium carbonate in ethanol 24 h; Ambient temperature;

1: K2CO3 / ethanol / 24 h / Ambient temperature 2: Sn, conc. HCl / acetic acid / 1.5 h / 100 - 105 °C View Scheme

1: 96 percent / concd. HCl, acetic acid, Zn / 0.25 h / 0 °C 2: 90 percent / concd. HCl / ethanol 3: 1.) aq. HCl, sodium nitrite, 2.) 48percent aq. HBF4 / 1.) 0 deg C, 5 min, 2.) 0 deg C, 30 min 4: 13 percent / 48percent aq. HBF4 / 1 h / Irradiation View Scheme

1: 96 percent / concd. HCl, acetic acid, Zn / 0.25 h / 0 °C 2: 90 percent / concd. HCl / ethanol 3: 1.) aq. HCl, sodium nitrite, 2.) aq. KI / 1.) 0 deg C, 10 min View Scheme

1: 96 percent / concd. HCl, acetic acid, Zn / 0.25 h / 0 °C 2: 90 percent / concd. HCl / ethanol 3: 1.) aq. HCl, sodium nitrite, 2.) aq. KI / 1.) 0 deg C, 10 min 4: 88 percent / Mg/CH3I / tetrahydrofuran / 21 h / Heating View Scheme