hydrogenchloride in methanol; water 12 h; Reflux;

1.1: copper(I) oxide; copper; potassium carbonate / diethylene glycol dimethyl ether / 5 h / Reflux 2.1: Eaton's reagent / 0.83 h / 80 °C 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere 3.2: 2 h / 20 °C / Inert atmosphere 4.1: hydrogenchloride / ethanol; water / 12 h / Reflux View Scheme

1.1: copper(I) oxide; copper; potassium carbonate / diethylene glycol dimethyl ether / 5 h / Reflux 2.1: Eaton's reagent / 0.83 h / 80 °C 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere 3.2: 2 h / 20 °C / Inert atmosphere 4.1: hydrogenchloride / ethanol; water / 12 h / Reflux View Scheme

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethanol; water / 12 h / Reflux View Scheme

1.1: Eaton's reagent / 0.83 h / 80 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere 3.1: hydrogenchloride / ethanol; water / 12 h / Reflux View Scheme

1.1: copper(I) oxide; copper; potassium carbonate / diethylene glycol dimethyl ether / 5 h / Reflux 2.1: Eaton's reagent / 0.83 h / 80 °C 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere 3.2: 2 h / 20 °C / Inert atmosphere 4.1: hydrogenchloride / ethanol; water / 12 h / Reflux View Scheme

1.1: copper(I) oxide; copper; potassium carbonate / diethylene glycol dimethyl ether / 5 h / Reflux 2.1: Eaton's reagent / 0.83 h / 80 °C 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere 3.2: 2 h / 20 °C / Inert atmosphere 4.1: hydrogenchloride / ethanol; water / 12 h / Reflux View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / 0 °C / |Inert atmosphere 1.2: 1 h / 0 - 20 °C / |Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / |Inert atmosphere 2.2: 1 h / 20 °C / |Inert atmosphere 3.1: sulfuric acid / butan-1-ol / 24 h / |Reflux 4.1: [2,2']bipyridinyl; copper(l) iodide; oxygen / N,N-dimethyl acetamide / 12 h / 160 °C / |Sealed tube 5.1: hydrogenchloride / methanol; water / 12 h / |Reflux View Scheme

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / |Inert atmosphere 1.2: 1 h / 20 °C / |Inert atmosphere 2.1: sulfuric acid / butan-1-ol / 24 h / |Reflux 3.1: [2,2']bipyridinyl; copper(l) iodide; oxygen / N,N-dimethyl acetamide / 12 h / 160 °C / |Sealed tube 4.1: hydrogenchloride / methanol; water / 12 h / |Reflux View Scheme

1: sulfuric acid / butan-1-ol / 24 h / |Reflux 2: [2,2']bipyridinyl; copper(l) iodide; oxygen / N,N-dimethyl acetamide / 12 h / 160 °C / |Sealed tube 3: hydrogenchloride / methanol; water / 12 h / |Reflux View Scheme