(i) NaNO2, aq. HCl, (ii) NaBH4, aq. NaHCO3; Multistep reaction;

1.1: conc. aq. HCl; NaNO2 / 0.25 h / 0 °C 1.2: 84 percent / KI / H2O / Heating 2.1: 91 percent / Fe3(CO)12; methanol / toluene / 3.5 h / Heating 3.1: 83 percent / tetrakis(triphenylphosphine) palladium(0) / dimethylformamide / 2 h / 80 °C 4.1: conc. aq. HCl; NaNO2 / 0.25 h / 0 °C 4.2: 64 percent / KI / H2O / Heating 5.1: 78 percent / 3percent aq. H2O2 / 4 h / 50 °C 6.1: 82 percent / BBr3 / CH2Cl2 / 4 h / Heating View Scheme

1: 1.) 48percent aq. HBr, aq. NaNO2, 2.) 48percent aq. HBr, CuBr / 2.) reflux 2: 93 percent / dimethylformamide / 5 h / Heating View Scheme

Diazotization.Umsetzung der Diazoniumsalzloesung mit CuBr;

boron trifluoride-diethyl ether complex in ethylene glycol dimethyl ether

sulfuric acid; water; sodium nitrite Diazotization.Behandeln mit Wasser;

1: With hydrogenchloride; sodium nitrite T=0°C; Diazotization; 0.25 h; 2: With potassium iodide in water Substitution; Heating; Further stages.;

in acetonitrile T=25°C; Kinetics;

1: Diazotization.Umsetzung des Diazoniumsalzes mit CuCl 2: hydrochloric acid / 165 °C 3: HNO3+H2SO4 / 50 °C 4: alcohol; ammonia View Scheme

1: Diazotization.Umsetzung des Diazoniumsalzes mit CuCl 2: hydrochloric acid / 165 °C View Scheme