1: With hydrogenchloride; sodium nitrite in water T=0°C; 0.0833333 h; 2: With copper(I) bromide in water T=0 - 90°C;

1: 61.2 percent / n-BuLi, 2-bromobenzyl bromide / tetrahydrofuran / 1.) -78 deg C, 0.5 h; r.t., 1 h, 2.) -78 deg C, 1 h; r.t., 1 h 2: 85.2 percent / conc. H2SO4 / aq. acetic acid / 3 h / Heating View Scheme

nitric acid

1: (i) NaNO2, aq. HCl, (ii) CuCl 2: aq. KMnO4 View Scheme

1: amalgamated aluminium / durch Bromieren 2: HNO3 View Scheme

1: amalgamated aluminium / durch Chlorieren 2: HNO3 View Scheme

1: With borane-THF in tetrahydrofuran T=0 - 20°C; 2: With water; sodium carbonate in tetrahydrofuran

potassium carbonate; copper(I) oxide; copper in 2-ethoxy-ethanol T=130°C; 24 h;

1.1: thionyl chloride / toluene / 20 °C / Reflux 2.1: AlCl3, aluminium chloride / 0 - 60 °C 3.1: N,N-dimethyl-formamide / 7 h / 110 °C 4.1: sulfuric acid / water / 3 h / 160 °C 5.1: thionyl chloride / benzene / 3 h / Reflux 6.1: methanol; sodium tetrahydroborate / tert-butyl alcohol / Reflux 7.1: toluene-4-sulfonic acid / benzene / 2 h / Reflux 8.1: triphenylphosphine; nickel dichloride; zinc / acetonitrile / 0.5 h / 20 °C 8.2: 8 h / Reflux View Scheme

1.1: thionyl chloride / toluene / 20 °C / Reflux 2.1: AlCl3, aluminium chloride / 0 - 60 °C 3.1: N,N-dimethyl-formamide / 7 h / 110 °C 4.1: sulfuric acid / water / 3 h / 160 °C 5.1: thionyl chloride / benzene / 3 h / Reflux 6.1: methanol; sodium tetrahydroborate / tert-butyl alcohol / Reflux 7.1: toluene-4-sulfonic acid / benzene / 2 h / Reflux 8.1: triphenylphosphine; nickel dichloride; zinc / acetonitrile / 0.5 h / 20 °C 8.2: 8 h / Reflux 9.1: sodium hydride / dimethyl sulfoxide; paraffin oil / 0.17 h / 20 °C / Inert atmosphere 9.2: 0.83 h / 40 °C View Scheme