tetrabutyl ammonium fluoride in dimethyl sulfoxide T=20°C; 1 h;

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

1.1: BuLi / tetrahydrofuran; hexane / 2 h / -75 °C 1.2: 80 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane / 1 h / -75 °C 2.1: 79 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 2 h / 150 °C 3.1: 77 percent / HCOONH4 / Pd/C / octan-1-ol / 4 h / 75 °C View Scheme

1.1: BuLi / tetrahydrofuran; hexane / 2 h / -75 °C 1.2: 80 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane / 1 h / -75 °C 2.1: 79 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 2 h / 150 °C View Scheme

1: 3-chloro-2-fluoropyridine With n-butyllithium; diisopropylamine in tetrahydrofuran; hexane T=-78°C; 1 h; 2: carbon dioxide in tetrahydrofuran; hexane T=-78 - 20°C;

1: With n-butyllithium in tetrahydrofuran; hexane T=-75°C; 2 h; 2: With 1,2,2-trifluoro-trichloroethane in tetrahydrofuran; hexane T=-75°C; 1 h;