Dimethylformamide → 3-Chloro-2-(2,4-dimethylphenoxy)-1,4-dimethyl-5-nitrobenzene

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Reaction Steps

To a flask equipped with condenser, stirrer, under nitrogen, was added 3,6-dimethyl-4,5-dichloronitrobenzene (50 g, 0.23 mol), 2,4-dimethylphenol (38.5 g, 0.32 mol), potassium carbonate (50 g, 0.36 mol), and dimethylformamide (125 ml). The resulting mixture was heated at 90°~100° for 72 hours. It was then cooled, filtered, and concentrated to give dark oil. It was partitioned between toluene (300 ml) and 4% sodium hydroxide (250 ml) and then separated. The organic layer was washed with water and brine, dried (Na2SO4) and concentrated to give dark oil. Solid was formed after the oil was trituated with hexane. The solid was washed with cold hexane and vacuum dried to give a tan powder (47.8 g, 0.16 mol); mp 78°~80°.

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