Iodine → HCID 59224659, compound

Participants

Reaction Steps

A methanol solution (12 ml) of 2-ethoxy-4-methylbenzoic acid methyl ester (1.1 g, 5.9 mmol) obtained in Step 2 above, silver trifluoromethanesulfonate (1.7 g, 6.6 mmol), and iodine (1.7 g, 6.6 mmol) was stirred at room temperature for 2.5 hours. The reaction solution was concentrated under reduced pressure. Ethyl acetate (100 ml) was added to the resulting residue. Insoluble material was separated by filtration, and washed with ethyl acetate (100 ml). The filtrate and washing solution were combined together, and sequentially washed twice with an 5% aqueous sodium thiosulfate solution (100 ml), and with a saturated aqueous sodium chloride solution (100 ml). Then, the washed solution was dried over anhydrous sodium sulfate. After the anhydrous sodium sulfate was removed by filtration, the solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=10:1) to yield 5-iodo-2-ethoxy-4-methylbenzoic acid methyl ester (1.8 g) as a pale yellow oily material.

Provenance & Evidence