sodium hydroxide in ethanol; water T=70°C; 16 h;

in 1,2-dichloro-benzene T=200°C; Inert atmosphere;

1: 45 percent / H2, MgO / 10percent Pd on carbon / ethanol / 760 Torr / Ambient temperature 2: 30 percent / 10percent Pd on carbon / 0.25 h / 200 °C View Scheme

1.1: boron trifluoride diethyl etherate / tetrahydrofuran / 0.08 h / -15 - -10 °C / Inert atmosphere 1.2: 0.5 h / -15 - 5 °C / Inert atmosphere 1.3: 2 h / 20 °C / Inert atmosphere 2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diisopropylamine / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere 2.2: 50 °C / Inert atmosphere 3.1: methanol; potassium carbonate / tetrahydrofuran / 20 °C 4.1: 1,2-dichloro-benzene / 200 °C / Inert atmosphere View Scheme

1.1: N-bromosuccinmide; zirconium tetrachloride / dichloromethane / Inert atmosphere 2.1: boron trifluoride diethyl etherate / tetrahydrofuran / 0.08 h / -15 - -10 °C / Inert atmosphere 2.2: 0.5 h / -15 - 5 °C / Inert atmosphere 2.3: 2 h / 20 °C / Inert atmosphere 3.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diisopropylamine / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere 3.2: 50 °C / Inert atmosphere 4.1: methanol; potassium carbonate / tetrahydrofuran / 20 °C 5.1: 1,2-dichloro-benzene / 200 °C / Inert atmosphere View Scheme

1.1: potassium tert-butylate / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 16 h / -78 - 20 °C 2.1: copper(l) iodide; potassium carbonate; N-methyl-2-(methylamino)ethylamine / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 3.1: sodium hydroxide / ethanol; water / 16 h / 70 °C View Scheme