1: 71 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 6 h / 125 °C 2: HCOONH4 / Pd/C / octan-1-ol / 6 h / 45 °C View Scheme

1.1: 71 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 6 h / 125 °C 2.1: HCOONH4 / Pd/C / octan-1-ol / 6 h / 45 °C 3.1: BuLi; i-Pr2NH / tetrahydrofuran; hexane / 2 h / -75 °C 3.2: 68 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane / 1 h View Scheme

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

1.1: 72 percent / aq. CuSO4 / Heating 2.1: BuLi / tetrahydrofuran; hexane 2.2: 78 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane View Scheme

1.1: 87 percent / hydrazine monohydrate / ethanol / 20 h / Heating 2.1: 72 percent / aq. CuSO4 / Heating 3.1: BuLi / tetrahydrofuran; hexane 3.2: 78 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane View Scheme

potassium fluoride; anhydrous tetramethylammonium chloride in dimethyl sulfoxide T=125°C; 6 h;