Reaction #167585

Reaction equation

(3,3,4,4,4-Pentafluoro-butane-1-sulfonyl)-acetonitrile

trifluoro-methanesulfonic acid 2-trifluoromethylsulfanyl-ethyl ester

K2CO3

→

2-(3,3,4,4,4-Pentafluoro-butane-1-sulfonyl)-4-trifluoromethylsulfanyl-butyronitrile

Solvents

1,2-dimethoxyethane

H2O

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate (2×50 mL)
2. 2
   WashThe combined organic extracts were washed with brine (100 mL)
3. 3
   Dryingdried over Na2SO4
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   OtherThe residue was purified by column chromatography (SiO2, hexanes/EtOAc 19:1)
6. 6
   Otherto afford compound II-1 (0.28 g, 37%) as a white solid

Procedure

A mixture of (3,3,4,4,4-Pentafluoro-butane-1-sulfonyl)-acetonitrile (WO2007/060839) (0.50 g, 1.99 mmol), trifluoro-methanesulfonic acid 2-trifluoromethylsulfanyl-ethyl ester (WO 2007/147888) (0.55 g, 1.99 mmol), and K2CO3 (0.82 g, 5.97 mmol) in 1,2-dimethoxyethane (20 mL) was stirred under nitrogen at room temperature overnight. The reaction mixture was diluted with H2O (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, hexanes/EtOAc 19:1) to afford compound II-1 (0.28 g, 37%) as a white solid.

Source