T=25°C; 20 h; Irradiation;

T=25°C; 20 h;

1: 1.) Mg, I2, ZnCl2, 2.) PdCl2(PPh3)2 / 1.) Et2O, 1 h, 2.) Et2O, RT, 30 min 2: conc. H2SO4 / 0.5 h / Heating 3: 1.) LiAlH4, 2.) aq. NaOH / 1.) THF, 0 deg C, 30 min, 2.) RT, 1 h 4: Et3N, 4-dimethylaminopyridine / dimethylformamide / 2 h 5: 94 percent / AD-mix-β / 2-methyl-propan-2-ol; H2O / 8 h / 0 °C 6: pyridine / Ambient temperature 7: LiClO4 / acetonitrile / 16 h / 100 °C 8: Et3N / CH2Cl2 / 12 h / Ambient temperature 9: 92 percent / PPh3, diethyl azodicarboxylate / toluene / Ambient temperature 10: 83 percent / 4 N HCl / dioxane / 3 h / 60 °C View Scheme

1: NaH / dimethylformamide 2: Na2WO4; H2O2 / methanol 3: NaBH4 / methanol; tetrahydrofuran 4: 97 percent / TFA / tetrahydrofuran / 0.5 h / 0 °C 5: 86 percent / Zn; acetone / acetic acid / 2.5 h / 25 °C View Scheme

magnesium 1.) ether, 2.) ether, -15 deg C; Multistep reaction;

nitric acid T=50°C; 0.166667 h;

1.1: Mg / iodine / tetrahydrofuran / 2 h / Heating 1.2: tetrahydrofuran / 2 h / 0 - 20 °C 2.1: pyridinium chlorochromate / CH2Cl2 / 0.33 h / 20 °C View Scheme

1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 18 h / 85 °C 2: palladium on activated charcoal; hydrogen / methanol / 18 h / 20 °C 3: trifluoroacetic acid / dichloromethane / 5 h / 0 - 20 °C View Scheme

1: 4-bromo-1,2-dichloro-benzene With n-butyllithium in diethyl ether; hexane T=-78 - 0°C; 2 h; 2: 2-amino-5-chloro-benzoic acid in tetrahydrofuran; diethyl ether; hexane T=0°C; 2 h; Further stages;