oxalyl dichloride in DMF (N,N-dimethyl-formamide); dichloromethane T=20 - 25°C;

N,N-dimethyl-formamide in dichloromethane 14 h;

1: HNO3 2: PCl5 / 130 - 140 °C View Scheme

1: man ersetzt die NH2-Gruppe durch Chlor, reduziert mit Zinn und Salzsaeure und ersetzt die neugebildete NH2-Gruppe durch Brom 2: HNO3 3: PCl5 / 130 - 140 °C View Scheme

1: AlCl3, aluminium chloride / dichloromethane / 1 h / -5 - 0 °C 2: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / -20 - 20 °C View Scheme

AlCl3, aluminium chloride in dichloromethane T=0°C; 1 h;

1: o-methylmethoxybenzene With AlCl3, aluminium chloride in dichloromethane T=-5 - 0°C; 2: 5-bromo-2-chlorobenzoyl chloride in dichloromethane T=0 - 5°C;

AlCl3 in dichloromethane; N,N-dimethyl-formamide

N-ethyl-N,N-diisopropylamine in dichloromethane T=0 - 20°C; 19 h;

1.1: AlCl3, aluminium chloride / dichloromethane / 1 h / -5 - 20 °C / |Inert atmosphere 1.2: 2 h / -5 - 0 °C / |Inert atmosphere 2.1: AlCl3, aluminium chloride; sodium tetrahydroborate / tetrahydrofuran / 18 h / 5 - 20 °C / |Inert atmosphere 3.1: boron tribromide / dichloromethane / -10 - 0 °C / |Inert atmosphere 4.1: triethylamine / acetonitrile / 2 h / 5 - 15 °C 5.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.5 h / -65 °C / |Inert atmosphere 5.2: 3 h / -65 - -55 °C 5.3: 16 h / 20 - 25 °C 6.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 2 h / -30 - -10 °C / |Inert atmosphere 7.1: caesium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 12 h / 40 °C / |Inert atmosphere View Scheme