Iodine → HCID 59224659, compound

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.

1. concentrationThe reaction solution was concentrated under reduced pressure
2. additionEthyl acetate (100 ml) was added to the resulting residue
3. customInsoluble material was separated by filtration
4. washwashed with ethyl acetate (100 ml)
5. washThe filtrate and washing solution
6. washsequentially washed twice with an 5% aqueous sodium thiosulfate solution (100 ml)
7. dry with materialThen, the washed solution was dried over anhydrous sodium sulfate
8. customAfter the anhydrous sodium sulfate was removed by filtration
9. concentrationthe solution was concentrated under reduced pressure
10. customThe resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=10:1)

ORD record

ord-a4578fcc30d34320b584ba30770abd0f

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362236B2