AlCl3, aluminium chloride in toluene T=100°C; 10 h; Inert atmosphere;

1: sodium / diethyl ether / 18 h / 0 - 20 °C 2: acetic acid; hydrogenchloride / 0.5 h / |Reflux 3: methanol / 3 h / |Reflux 4: iodine; pyridine / dichloromethane / 20 h / 20 °C 5: AlCl3, aluminium chloride / toluene / 10 h / 100 °C / |Inert atmosphere View Scheme

1: acetic acid; hydrogenchloride / 0.5 h / |Reflux 2: methanol / 3 h / |Reflux 3: iodine; pyridine / dichloromethane / 20 h / 20 °C 4: AlCl3, aluminium chloride / toluene / 10 h / 100 °C / |Inert atmosphere View Scheme

1: methanol / 3 h / |Reflux 2: iodine; pyridine / dichloromethane / 20 h / 20 °C 3: AlCl3, aluminium chloride / toluene / 10 h / 100 °C / |Inert atmosphere View Scheme

1: iodine; pyridine / dichloromethane / 20 h / 20 °C 2: AlCl3, aluminium chloride / toluene / 10 h / 100 °C / |Inert atmosphere View Scheme

1: 3-Methylpyridine / anhydrous xylene / 24 h / |Reflux 2: sodium carbonate; palladium on activated charcoal / ethylene glycol dimethyl ether; water / 1 h / 45 °C 3: toluene-4-sulfonic acid / methanol; tetrahydrofuran / 1 h / 60 °C 4: potassium carbonate / acetone / 20 °C View Scheme