Methanol → 3-(Trifluoromethylthio)phenylacetic acid methyl ester

Temperature

25 °C

A solution of 3-(trifluoromethylthio)phenylacetic acid (5.00 g, 21.17 mmol) in methanol (50 mL) was treated slowly with 10 drops of concentrated sulfuric acid. The resulting reaction mixture was heated under reflux for 18 h. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo to remove methanol. The residue was diluted with ethyl acetate (100 mL). The organic phase was washed with a saturated aqueous sodium bicarbonate solution (1×100 mL), dried over magnesium sulfate, and filtered. The filtrate was concentrated in vacuo to afford (3-trifluoromethylsulfanyl-phenyl)-acetic acid methyl ester (5.28 g, 99%) as a pale yellow oil which was used without further purification: EI-HRMS m/e calcd for C10H9F3O2S (M+) 250.0275, found 250.0274.

1. customThe resulting reaction mixture
2. temperaturewas heated
3. temperatureunder reflux for 18 h
4. concentrationconcentrated in vacuo
5. customto remove methanol
6. additionThe residue was diluted with ethyl acetate (100 mL)
7. washThe organic phase was washed with a saturated aqueous sodium bicarbonate solution (1×100 mL)
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-90bc7bf27e314ee882fbbfc7ef05ab75

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610846B1