sodium carbonate; p-benozquinone; bis(benzonitrile)palladium(II) dichloride in 1,4-dioxane T=80°C; 3 h;

1: triethylamine / dichloromethane / 1 h / 0 - 5 °C / |Inert atmosphere 2: AlCl3, aluminium chloride / nitrobenzene / 5 h / 140 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 2 h / 25 - 30 °C 4: bromine / dichloromethane / 1 h / 25 - 30 °C 5: AlCl3, aluminium chloride / dichloromethane / 15 - 20 °C 6: triethylamine / dichloromethane / 2 h / 25 - 30 °C 7: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C 8: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C View Scheme

1: AlCl3, aluminium chloride / nitrobenzene / 5 h / 140 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 2 h / 25 - 30 °C 3: bromine / dichloromethane / 1 h / 25 - 30 °C 4: AlCl3, aluminium chloride / dichloromethane / 15 - 20 °C 5: triethylamine / dichloromethane / 2 h / 25 - 30 °C 6: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C 7: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C View Scheme

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 2 h / 25 - 30 °C 2: bromine / dichloromethane / 1 h / 25 - 30 °C 3: AlCl3, aluminium chloride / dichloromethane / 15 - 20 °C 4: triethylamine / dichloromethane / 2 h / 25 - 30 °C 5: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C 6: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C View Scheme

1: bromine / dichloromethane / 1 h / 25 - 30 °C 2: AlCl3, aluminium chloride / dichloromethane / 15 - 20 °C 3: triethylamine / dichloromethane / 2 h / 25 - 30 °C 4: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C 5: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C View Scheme

1: AlCl3, aluminium chloride / dichloromethane / 15 - 20 °C 2: triethylamine / dichloromethane / 2 h / 25 - 30 °C 3: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C 4: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C View Scheme

1: triethylamine / dichloromethane / 2 h / 25 - 30 °C 2: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C 3: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C View Scheme

1: triethylamine / dichloromethane / 1 h / 0 - 5 °C / |Inert atmosphere 2: AlCl3, aluminium chloride / nitrobenzene / 5 h / 140 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 2 h / 25 - 30 °C 4: bromine / dichloromethane / 1 h / 25 - 30 °C 5: AlCl3, aluminium chloride / dichloromethane / 15 - 20 °C 6: triethylamine / dichloromethane / 2 h / 25 - 30 °C 7: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C 8: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C View Scheme

1: 87 percent / K2CO3 / dimethylformamide / 3.5 h / 92 - 94 °C 2: 80 percent / NaOH / Heating 3: acetic anhydride; sodium acetate; acetic acid / 3 h / Heating View Scheme

1: 87 percent / K2CO3 / dimethylformamide / 3.5 h / 92 - 94 °C 2: 80 percent / NaOH / Heating 3: acetic anhydride; sodium acetate; acetic acid / 3 h / Heating View Scheme