manganese(IV) oxide in dichloromethane T=52°C; 2 h;

1: 5-Fluoro-benzo[b]thiophene With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 1 h; 2: N,N-dimethyl-formamide in tetrahydrofuran; hexane T=-78°C; 1 h;

1.1: 53 percent / potassium carbonate / dimethylformamide / 20 h / 20 - 60 °C 2.1: 99 percent / KOH / ethanol; H2O / 1.5 h / Heating 3.1: 92 percent / copper; quinoline / 2 h / 185 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 99 percent / tetrahydrofuran; hexane / 1 h / -78 °C View Scheme

1.1: 92 percent / copper; quinoline / 2 h / 185 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 99 percent / tetrahydrofuran; hexane / 1 h / -78 °C View Scheme

1.1: 99 percent / KOH / ethanol; H2O / 1.5 h / Heating 2.1: 92 percent / copper; quinoline / 2 h / 185 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: 99 percent / tetrahydrofuran; hexane / 1 h / -78 °C View Scheme

1: diisobutylaluminium hydride / tetrahydrofuran / -70 - -10 °C 2: manganese(IV) oxide / dichloromethane / 2 h / 52 °C View Scheme