Chlorobenzene → Ethyl 4-(3-fluoro-4-nitrophenoxy)pyridine-2-carboxylate

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To ethyl 4-chloropyridine-2-carboxylate (19.4 g) were added 3-fluoro-4-nitrophenol (24.7 g) and chlorobenzene (7.0 ml), and the % mixture was stirred and heated at 120° C. under a nitrogen atmosphere for 4 hours. The reaction mixture was cooled to room temperature. After adding ethyl acetate (400 ml) and a saturated aqueous solution of sodium carbonate (400 ml), the mixture was further stirred at room temperature for 27 hours. Stirring was suspended and the aqueous layer was separated off. A saturated aqueous solution of sodium carbonate was further added to the organic layer and the mixture was, stirred at room temperature for 2 days. Stirring was suspended, and the aqueous layer was separated off. The aqueous layer was extracted with ethyl acetate (300 ml). The organic layers were combined and washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:heptane:ethyl acetate=2:1 to 1:1, then ethyl acetate). The fractions containing the target compound were concentrated to give the title compound as a brown oil (12.9 g, 40.2%).

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