Water → 1-Chloro-4-ethoxy-2-nitrobenzene

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To a solution of 4-chloro-3-nitrophenol (5.21 g, 30 mmol) in acetone (60 ml) were added ethyl iodide (5.94 g, 38 mmol) and potassium carbonate (4.53 g, 33 mmol), followed by stirring at 50° C. for 5 hours. After allowing to stand overnight, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [eluent; ethyl acetate-hexane (1:4)] to give the title compound (5.72 g).

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