Iodine → Methyl 5-iodo-2-methoxy-4-methylbenzoate

Participants

Reaction Steps

A methanol solution (28 ml) of 2-methoxy-4-methylbenzoic acid methyl ester (1.2 g, 7.0 mmol) obtained in Step 1 above, silver trifluoromethanesulfonate (2.0 g, 7.8 mmol), and iodine (2.0 g, 7.8 mmol) was stirred at room temperature for 1.5 hour. The reaction solution was concentrated under reduced pressure. The resulting pale yellow solid was separated by filtration, and washed with ethyl acetate (300 ml). The washing solution was sequentially washed with 5% aqueous sodium thiosulfate solution (100 ml), and a saturated aqueous sodium chloride solution (100 ml). Then, the solution was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=2:1) to yield 5-iodo-2-methoxy-4-methylbenzoic acid methyl ester (1.9 g) as a pale yellow solid material.

Provenance & Evidence