[Bmim]Br3 T=50°C; 2.5 h; regioselective reaction;

ammonia; water; copper(II) sulfate

1: 1-bromo-3-(propan-2-yl)benzene With magnesium in tetrahydrofuran T=50 - 60°C; 2: carbon dioxide in tetrahydrofuran 0.666667 h; 3: With hydrogenchloride in tetrahydrofuran; water

1: pyridine / 190 °C 2: aqueous sulfuric acid View Scheme

1: (i) Mg, Et2O, (ii) /BRN= 1900390/, (iii) aq. HCl 2: SOCl2 View Scheme

1.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / |Inert atmosphere; |Reflux 1.2: 1 h / |Inert atmosphere 2.1: phosphorus tribromide / tetrahydrofuran / 0 °C / |Inert atmosphere 3.1: magnesium; dilithium tetrachlorocuprate / tetrahydrofuran / 2 h / 0 °C / |Inert atmosphere 4.1: o,o'-dichloro-BINOL; antimony(V) pentachloride / dichloromethane / 0.25 h / -78 °C / |Inert atmosphere 5.1: water; potassium permanganate; sodium periodate; sodium carbonate / tert-butyl alcohol / 12 h / 23 °C / |Inert atmosphere View Scheme

1: 1-bromo-3-(propan-2-yl)benzene With n-butyllithium in tetrahydrofuran T=-70°C; 0.75 h; Inert atmosphere; 2: tri-isopropoxy-borane in tetrahydrofuran T=-70 - 0°C; 2 h; Inert atmosphere; 3: With hydrogenchloride in tetrahydrofuran; water T=-20°C;

1: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 2 h; 2: With tri-isopropoxy-borane in tetrahydrofuran; hexane T=-78 - 20°C; 2 h; 3: With hydrogenchloride

magnesium in tetrahydrofuran 0.75 h; Heating / reflux;

diethyl ether; lithium anschliessend Erwaermen mit Acetaldehyd;