sodium hydroxide; zinc T=25°C; 6 h;

copper(II) sulfate Heating;

1: 87 percent / hydrazine monohydrate / ethanol / 20 h / Heating 2: 72 percent / aq. CuSO4 / Heating View Scheme

1: 97 percent / phosphoryl tribromide / dimethylformamide / 2 h / 130 °C 2: 92 percent / aq. sodium hydroxide; zinc powder / 6 h / 25 °C View Scheme

1.1: butyllithium; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran / 0.25 h / -75 °C 1.2: methanol 2.1: 92 percent / aq. sodium hydroxide; zinc powder / 6 h / 25 °C View Scheme

1.1: BuLi / tetrahydrofuran; hexane 1.2: 78 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane 2.1: 71 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 6 h / 125 °C 3.1: HCOONH4 / Pd/C / octan-1-ol / 6 h / 45 °C View Scheme

potassium phosphate; copper(l) iodide; 1,10-phenanthroline; iodine; lithium tert-butylate in 1,4-dioxane T=115°C; 6 h; Inert atmosphere; regioselective reaction;

1.1: BuLi / tetrahydrofuran; hexane 1.2: 78 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane 2.1: 71 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 6 h / 125 °C 3.1: HCOONH4 / Pd/C / octan-1-ol / 6 h / 45 °C 4.1: BuLi; i-Pr2NH / tetrahydrofuran; hexane / 2 h / -75 °C 4.2: 68 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane / 1 h View Scheme

1.1: BuLi / tetrahydrofuran; hexane 1.2: 78 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane 2.1: 71 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 6 h / 125 °C View Scheme

1: With n-butyllithium in tetrahydrofuran; hexane 2: With 1,2,2-trifluoro-trichloroethane in tetrahydrofuran; hexane