1: 2-chloromethyl-pyridine hydrochloride With potassium carbonate in N,N-dimethyl-formamide T=20°C; 0.5 h; 2: 2-chloro-4-nitrophenol With potassium iodide in N,N-dimethyl-formamide T=60°C; 12 h;

1: 2-hydroxymethyl-pyridine With sodium hydride in DMF (N,N-dimethyl-formamide) T=0°C; 0.25 h; 2: 1-chloro-2-fluoro-5-nitrobenzene 36 h;

potassium hydroxide in tetrahydrofuran T=20 - 25°C; 20 h; Product distribution / selectivity;

hydrogenchloride; caesium carbonate; sodium iodide in acetonitrile T=60°C; 5 h;

potassium hydroxide; Aliquatreg; 336 in water; toluene T=60°C;

in water; mineral oil

hydrogen; platinum on carbon in ethanol 3 h; Product distribution / selectivity;

1.1: iron; ammonium chloride / ethanol; water / 1 h / |Reflux 2.1: methanesulfonic acid / ethanol / 2 h / |Reflux 3.1: hydrogenchloride; water / |Reflux 4.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5 h / 40 °C 5.1: hydrogenchloride; water / 0 - 40 °C / |Inert atmosphere 5.2: 3 h / -20 °C View Scheme

1: iron; ammonium chloride / ethanol; water / 1 h / |Reflux 2: methanesulfonic acid / ethanol / 2 h / |Reflux 3: hydrogenchloride; water / |Reflux View Scheme