in tetrahydrofuran T=-40°C;

hydrogenchloride; sodium borohydride; boron trichloride; aluminium trichloride in 1,4-dioxane; dichloromethane; water

1: 76 percent / nitric acid; sulfuric acid; water / 0 °C 2: 57 percent / tetrahydrofuran / -40 °C View Scheme

n-butyllithium in tetrahydrofuran; hexane T=-75°C;

1: 7-bromo-5-fluoroindole With sec.-butyllithium in tetrahydrofuran; cyclohexane T=-75°C; 2: carbon dioxide in tetrahydrofuran; cyclohexane cooling;

tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide T=120°C; Inert atmosphere;

1.1: 48 percent / BuLi / tetrahydrofuran; hexane / -75 °C 2.1: 93 percent / BuLi / hexane; tetrahydrofuran / 25 °C 3.1: 2,2,6,6-tetramethylpiperidine; N,N,N',N'-pentamethyldiethylenetriamine; BuLi / tetrahydrofuran; hexane / 6 h / -75 °C 3.2: 62 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane / -75 - 25 °C 4.1: 94 percent / tetrabutylammonium fluoride hydrate / tetrahydrofuran / 25 °C View Scheme