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

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.

1. concentrationThe reaction solution was concentrated under reduced pressure
2. customThe resulting pale yellow solid was separated by filtration
3. washwashed with ethyl acetate (300 ml)
4. washThe washing solution was sequentially washed with 5% aqueous sodium thiosulfate solution (100 ml)
5. dry with materialThen, the solution was dried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe resulting crude product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=2:1)

ORD-Eintrag

ord-0528349d52c14f9a9006706679ef55cc

Quelldatensatz

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08362236B2