Water → Methyl 4-iodo-3-nitrobenzoate

Participants

Reaction Steps

To a solution of 4-iodo-3-nitrobenzoic acid (3 g, 10 mmol) in methanol (30 ml) cooled to 0° C., sulfuric acid (3.4 g, 34.6 mmol) is added slowly. The reaction mixture is warmed to room temperature and then refluxed (˜70° C.) for 8 hours. After cooling, the reaction mixture is neutralized with solid NaHCO3 and the salts are filtered. The filtrate is evaporated under reduced pressure. To the residue obtained, water (30 ml) is added and the mixture extracted with MTBE (30 ml×2). The combined organic phase is washed with brine, dried using anhydrous sodium sulfate and filtered. After evaporating the solvent under reduced pressure, 4-iodo-3-nitro-benzoic acid methyl ester is obtained as a yellow solid (2.67 g, 85% yield, 98% HPLC).

Provenance & Evidence