Mn(OAc)3•2H2O; 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane T=22°C; 1 h;

1: 4-bromo-N,N-dimethyl-aniline With magnesium in tetrahydrofuran T=20°C; Inert atmosphere; 2: N-methoxy-N-methylpropionamide in tetrahydrofuran T=-20 - 20°C; Inert atmosphere; 3: With water in tetrahydrofuran

1: With copper(I) bromide in tetrahydrofuran T=60°C; 4 h; 2: With sulfuric acid in tetrahydrofuran; water 1 h; Reflux;

1: N-cyclohexyl-4-(dimethylamino)benzamide With 2-fluoro-pyridine; trifluoromethylsulfonic anhydride in dichloromethane T=-78 - 0°C; Inert atmosphere; 2: ethylmagnesium bromide in dichloromethane T=-78°C; 0.416667 h; Inert atmosphere; 3: With hydrogenchloride; water in tetrahydrofuran; dichloromethane T=65°C; 2 h; Inert atmosphere; chemoselective reaction;

methanol anschliessend Erhitzen mit Alkalilauge unter Durchleiten von Wasserdampf;

1.1: iodine; zinc / tetrahydrofuran / 1 h / Inert atmosphere 1.2: 0 - 22 °C / Inert atmosphere 2.1: manganese triacetate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 22 °C / Inert atmosphere View Scheme

sodium hydride in N,N,N',N',N'',N''-hexamethylphosphoric triamide T=20°C; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

T=150°C; 63 h;

ammonium acetate in acetic acid T=50°C; P=7500600 Torr; 3 h; other pressure, other base, other substrates, other nitrocompound; Product distributionMechanism;

phosphorus pentoxide