1.1: pyridine / dichloromethane; acetonitrile / 3.5 h / 45 °C / |Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / |Inert atmosphere; |Cooling with ice 2.2: |Inert atmosphere 3.1: sodium hydride / 6.5 h / 20 °C / |Inert atmosphere 4.1: potassium tert-butylate / diethyl ether / 2 h / 40 - 45 °C / |Inert atmosphere 5.1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / water; dichloromethane / 20 °C 6.1: tetrakis(triphenylphosphine) palladium(0); morpholine / tetrahydrofuran / 20 °C 7.1: potassium carbonate; silver(I) acetate / 0.33 h / 90 - 95 °C 8.1: sodium methylate / methanol / 20 °C View Scheme

bromine in methanol T=-70°C; 3 h;

1: bromine / acetic acid / 5 h / 20 °C / |Cooling with ice 2: potassium permanganate; magnesium sulfate / water / 5.5 h / |Reflux 3: sodium hydroxide; water / 4 h / |Reflux View Scheme