hydrogen; triethylamine; palladium on activated charcoal in methanol T=25°C; P=760 Torr; 2 h;

phosphorus oxytribromide T=150°C; 0.5 h;

1: 2-bromo-3-fluoroquinoline With n-butyllithium; diisopropylamine in tetrahydrofuran; hexane T=-75°C; 2 h; 2: carbon dioxide in tetrahydrofuran; hexane

1: 2-bromo-3-fluoroquinoline With n-butyllithium; diisopropylamine in tetrahydrofuran; hexane T=-75°C; 2 h; 2: N,N-dimethyl-formamide in tetrahydrofuran; hexane 2 h;

1.1: diisopropylamine; butyllithium / tetrahydrofuran; hexane / 2 h / -75 °C 1.2: 98 percent / tetrahydrofuran; hexane / 2 h 2.1: 97 percent / BF3*OEt2 / CH2Cl2 / 24 h / 25 °C View Scheme

1.1: diisopropylamine; butyllithium / tetrahydrofuran; hexane / 2 h / -75 °C 1.2: 98 percent / tetrahydrofuran; hexane / 2 h 2.1: 97 percent / BF3*OEt2 / CH2Cl2 / 24 h / 25 °C 3.1: butyllithium / tetrahydrofuran; diethyl ether; hexane / 6 h / -100 °C 3.2: 94 percent / tetrahydrofuran; diethyl ether; hexane View Scheme