Sodium Iodide → 2-(5-Chloro-2-nitrophenoxy)-5-methoxybenzoic acid, methyl ester

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To a solution of 61.8 g of 2-hydroxy-5-methoxybenzoic acid, methyl ester in 700 ml DMF was added 14.96 g of a 60% suspension of sodium hydride in mineral oil. This was followed by addition of 50.88 g of sodium iodide, 64.64 g of copper(I)iodide, and 2.16 g of finely powdered copper metal. The mixture was heated to 85° C., for 15 minutes, then 71.7 g of 2,4-dichloronitrobenzene was added, and the reaction was stirred at 85° C. for 16 hours. The mixture was filtered, and the filtrate concentrated to an oily residue. Sodium thiosulfate, 400 ml of a 20% solution was added, followed by extraction with ethyl acetate (3×400 ml). The combined ethyl acetate extracts were washed with water (2×325 ml), dried over anhydrous sodium sulfate, then evaporated to afford a pale yellow solid, which was triturated with cyclohexane and filtered giving the title compound, mp 114°-116° C.

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