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 concentrated sulfuric acid (10 drops). The resulting reaction mixture was heated to 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 crude (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. temperatureto 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-0a99a0ca26974b9a8ceab315f9374496

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06528543B1