sulfuric acid 3 h; HeatingReflux; Product distribution / selectivity;

bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate; 6-diphenylphosphinomethyl-3-methyl-2-aminopyridine in toluene T=150°C; 1 h; Inert atmosphere;

chromium(VI) oxide in water; acetic acid T=20°C; 12 h;

1: SOCl2 / benzene / 2 h / Heating 2: methanol / 3 h / 0 °C 3: 25 percent / CrO3 / acetic acid; H2O; acetic acid / 12 h / 20 °C View Scheme

1: 98 percent / aluminium chloride / benzene / 4 h / 20 °C 2: 95 percent / Br2; KOH / H2O / 3 h / 55 °C 3: SOCl2 / benzene / 2 h / Heating 4: methanol / 3 h / 0 °C 5: 25 percent / CrO3 / acetic acid; H2O; acetic acid / 12 h / 20 °C View Scheme

1: 95 percent / Br2; KOH / H2O / 3 h / 55 °C 2: SOCl2 / benzene / 2 h / Heating 3: methanol / 3 h / 0 °C 4: 25 percent / CrO3 / acetic acid; H2O; acetic acid / 12 h / 20 °C View Scheme

1: methanol / 3 h / 0 °C 2: 25 percent / CrO3 / acetic acid; H2O; acetic acid / 12 h / 20 °C View Scheme

1: caesium carbonate; triphenylphosphine; palladium dichloride / tetrahydrofuran; water / 22 h / 85 °C / sealed tube; Inert atmosphere 2: bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate; 6-diphenylphosphinomethyl-3-methyl-2-aminopyridine / toluene / 1 h / 150 °C / Inert atmosphere View Scheme

1.1: sulfuric acid; water / methanol / 1 h / Reflux; Inert atmosphere 1.2: 3 h / Reflux; Inert atmosphere 2.1: caesium carbonate; triphenylphosphine; palladium dichloride / tetrahydrofuran; water / 22 h / 85 °C / sealed tube; Inert atmosphere 3.1: bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate; 6-diphenylphosphinomethyl-3-methyl-2-aminopyridine / toluene / 1 h / 150 °C / Inert atmosphere View Scheme

1.1: chromium(VI) oxide; sulfuric acid / 1.5 h / Cooling with ice; Inert atmosphere 2.1: sulfuric acid; water / methanol / 1 h / Reflux; Inert atmosphere 2.2: 3 h / Reflux; Inert atmosphere 3.1: caesium carbonate; triphenylphosphine; palladium dichloride / tetrahydrofuran; water / 22 h / 85 °C / sealed tube; Inert atmosphere 4.1: bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate; 6-diphenylphosphinomethyl-3-methyl-2-aminopyridine / toluene / 1 h / 150 °C / Inert atmosphere View Scheme