Malononitrile → (2,2,3,3,4,4,5,5-Octafluoropentyl)propanedinitrile
Reaction equation
FC(F)(F)S(O[CH2:7][C:8]([F:19])([F:18])[C:9]([F:17])([F:16])[C:10]([F:15])([F:14])[CH:11]([F:13])[F:12])(=O)=O.[C:22](#[N:26])[CH2:23][C:24]#[N:25].C(=O)([O-])[O-].[K+].[K+]>>[F:19][C:8]([F:18])([C:9]([F:16])([F:17])[C:10]([F:14])([F:15])[CH:11]([F:12])[F:13])[CH2:7][CH:23]([C:22]#[N:26])[C:24]#[N:25]Participants
4
Procedure
A mixture of compound 5b (15.0 g, 41.2 mmol), malononitrile (5.44 g, 82.4 mmol), and potassium carbonate (28.5 g, 206 mmol) in 1,2-dimethoxymethane (150 ml) was stirred overnight at room temperature under nitrogen. The reaction mixture was quenched with water (150 ml) and extracted with ethyl acetate (2×200 ml). The combined organic extracts were washed with brine (200 ml), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 85:15 hexanes/EtOAc) to provide 2-(2,2,3,3,4,4,5,5-Octafluoropentyl)malononitrile (5c) (7.5 g, 65%) as a white solid:
Workup
- customThe reaction mixture was quenched with water (150 ml)
- extractionextracted with ethyl acetate (2×200 ml)
- washThe combined organic extracts were washed with brine (200 ml)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography (silica gel, 85:15 hexanes/EtOAc)
Sources & evidence
- ORD record
- ord-56136604385748b694f8dc9c1b1fca33
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901170B2
Reaction notes
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