potassium hydroxide in methanol T=20°C; 1 h;

1: H2 / Pd/C / ethyl acetate / 192 h / 20 °C / 3102.89 Torr 2: Br2 3: o-chloranil / benzene / 24 h / Heating 4: 82 percent / KOH / methanol / 1 h / 20 °C View Scheme

1: Br2 2: o-chloranil / benzene / 24 h / Heating 3: 82 percent / KOH / methanol / 1 h / 20 °C View Scheme

1: o-chloranil / benzene / 24 h / Heating 2: 82 percent / KOH / methanol / 1 h / 20 °C View Scheme

1: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 4 h / 20 °C 2: pyridine / 16 h / 0 - 20 °C / Inert atmosphere 3: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere 4: sodium carbonate / methanol; water / 16 h / 20 °C View Scheme

1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere 2: sodium carbonate / methanol; water / 16 h / 20 °C View Scheme

1: pyridine / 16 h / 0 - 20 °C / Inert atmosphere 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere 3: sodium carbonate / methanol; water / 16 h / 20 °C View Scheme

(i) PCl5, (ii) NaNH2, liq. NH3; Multistep reaction;

1: (i) Mg, EtOH, toluene, (ii) /BRN= 3302933/, THF, (iii) H2SO4, AcOH 2: (i) PCl5, (ii) NaNH2, liq. NH3 View Scheme