Nitric Acid → Methyl 4-iodo-3-nitrobenzoate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A solution of 4-iodobenzoic acid methyl ester (5.24 g, 20.0 mmol) in sulfuric acid was treated with 1.43 mL of concentrated nitric acid in a dropwise fashion at 0° C. After 5 hours at room temperature, the reaction mixture was heated to 40° C. for 1 hour. The resulting orange solution was added to 100 g of ice, treated with 200 mL of ethyl acetate, shaken for 30 minutes, and filtered. The phases were separated and the aqueous layer was extracted with 200 mL of ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was passed through a column of silica gel (100% ethyl acetate) to give 2.0 g of 4-iodo-3-nitrobenzoic acid methyl ester as a yellow solid (33% yield).

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