bromine in acetic acid T=20°C;

potassium carbonate in acetone T=55°C;

1: 68 percent / pyridine / CH2Cl2 / 60 h / 20 °C 2: triethylamine; bis(triphenylphosphine)palladium(II) chloride / dimethylformamide / 12 h / 110 °C 3: 38.3 g / H2 / platinum oxide hydrate / aq. ethanol 4: 73 percent / aq. NaOH / ethanol / 6 h / 20 °C 5: oxalyl chloride / CH2Cl2 / 4 h / 20 °C 6: 4.1 g / aluminum chloride / CH2Cl2 / 2 h / Heating View Scheme

1: 68 percent / pyridine / CH2Cl2 / 60 h / 20 °C 2: triethylamine; bis(triphenylphosphine)palladium(II) chloride / dimethylformamide / 12 h / 110 °C 3: 38.3 g / H2 / platinum oxide hydrate / aq. ethanol 4: 73 percent / aq. NaOH / ethanol / 6 h / 20 °C View Scheme

potassium carbonate in dimethyl sulfoxide T=120°C; 32 h;

[(P{(C6H11)3})2Pd(Cl)2] in tetrahydrofuran T=50°C; 24 h; Inert atmosphere;

1: 68 percent / pyridine / CH2Cl2 / 60 h / 20 °C 2: triethylamine; bis(triphenylphosphine)palladium(II) chloride / dimethylformamide / 12 h / 110 °C 3: 38.3 g / H2 / platinum oxide hydrate / aq. ethanol View Scheme