1: With n-butyllithium in diethyl ether; hexane T=-70°C; 2 h; Inert atmosphere; 2: With tri-isopropoxy-borane in diethyl ether; hexane T=20°C; 16 h; Inert atmosphere;

iodine; copper

tetrakis(triphenylphosphine) palladium(0); potassium carbonate in methanol; toluene Suzuki Coupling; 24 h; Reflux;

1.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 2.5 h / -78 °C 1.2: 0.5 h / -78 - 0 °C 2.1: hydrogenchloride / water; ethyl acetate / 1 h / 0 °C 3.1: sodium carbonate / ethanol; water; toluene / 1 h / 20 °C 3.2: 5 h / 90 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C 1.2: 100 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C 2.1: 93 percent / BBr3 / CH2Cl2 / 16 h / 20 °C View Scheme

1: 49 percent / 99percent nitric acid, 96percent sulfuric acid / acetic anhydride / 0.17 h / -30 °C 2: 92 percent / dimethylformamide / 1 h / Ambient temperature 3: 91 percent / triethylamine, H2 / 10percent palladium on carbon / methanol / 1.5 h / 3800 Torr / Ambient temperature 4: 1.) triethylamine; 2.) 5percent HCl / 1.) CH2Cl2, refl., 30 min; 2.) 60 deg C, 3 h 5: 72 percent / pentan-1-ol / 2 h / Heating View Scheme