Hydrochloric Acid → Methyl 2-(3,3,3-trifluoropropylsulfonyl)acetate

To a solution of 10 g of methyl thioglycolate and 21 g of 1-iodo-3,3,3-trifluoropropane in 200 ml of N,N-dimethylformamide, 13 g of potassium carbonate was added under ice-cooling, and then stirred at room temperature for 20 hours. To the reaction mixture, 10% hydrochloric acid was added, followed by extraction with ethyl acetate. The organic layer was washed sequentially with 10% hydrochloric acid and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain a crude product comprising methyl (3,3,3-trifluoropropylthio)acetate. The obtained crude product was dissolved in 100 ml of glacial acetic acid, and 50 ml of peracetic acid (32% (w/w) acetic acid solution) was added thereto under ice-cooling. The mixture was stirred at 60° C. for 16 hours. In the middle of the reaction, the formation of a compound that was presumed to be in a sulfoxide form was confirmed by TLC (thin layer chromathgraphy) analysis. The reaction mixture was allowed to stand to cool to nearly room temperature, poured into water and then extracted with ethyl acetate. The organic layer was washed sequentially with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 14.1 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate.

1. temperaturecooling
2. extractionfollowed by extraction with ethyl acetate
3. washThe organic layer was washed sequentially with 10% hydrochloric acid
4. dry with materiala saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customto obtain a crude product
7. customThe obtained crude product
8. temperatureunder ice-cooling
9. stirringThe mixture was stirred at 60° C. for 16 hours
10. customIn the middle of the reaction
11. temperatureto cool to nearly room temperature
12. extractionextracted with ethyl acetate
13. washThe organic layer was washed sequentially with a saturated sodium hydrogen carbonate aqueous solution
14. dry with materiala saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate
15. concentrationconcentrated under reduced pressure

ORD record

ord-62b108dc5fa54d49a733eabd94894bcb

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247612B2