triethylamine in tetrahydrofuran T=60°C;

1: tin; hydrochloric acid View Scheme

1: concentrated sulfuric acid; concentrated nitric acid / das mit Aether isolierte Reaktionsprodukt unterwirft man der fraktionierten Destillation, wobei 4-Chlor-2-nitro-toluol bei 240-245grad uebergeht 2: tin; hydrochloric acid View Scheme

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1: potassium permanganate; magnesium sulfate 2: concentrated hydrochloric acid / Zers. des entstandenen Hydrochlorids mit Natriumacetat 3: Diazotization.Einw. von CuCl und HCl auf das Diazotierungsprodukt View Scheme

1.1: bromine / acetic acid / 5 h / 20 °C / |Cooling with ice 2.1: potassium permanganate; magnesium sulfate / water / 5.5 h / |Reflux 3.1: sodium hydroxide; water / 4 h / |Reflux 4.1: pyridine / dichloromethane; acetonitrile / 3.5 h / 45 °C / |Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / |Inert atmosphere; |Cooling with ice 5.2: |Inert atmosphere 6.1: sodium hydride / 6.5 h / 20 °C / |Inert atmosphere 7.1: potassium tert-butylate / diethyl ether / 2 h / 40 - 45 °C / |Inert atmosphere 8.1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / water; dichloromethane / 20 °C 9.1: tetrakis(triphenylphosphine) palladium(0); morpholine / tetrahydrofuran / 20 °C 10.1: potassium carbonate; silver(I) acetate / 0.33 h / 90 - 95 °C 11.1: sodium methylate / methanol / 20 °C View Scheme

1: ClSO3H; aqueous NH3 2: aqueous KMnO4 3: aqueous ethanol HCl View Scheme

1: potassium permanganate; magnesium sulfate 2: concentrated hydrochloric acid / Zers. des entstandenen Hydrochlorids mit Natriumacetat View Scheme

1: water; magnesium sulfate; potassium permanganate 2: hydrogen chloride View Scheme

sulfuric acid; nitric acid; acetic acid T=10 - 15°C;