Malononitrile → (3,4,4-Trifluoro-3-butenyl)malononitrile
Reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].Br[CH2:7][CH2:8][C:9]([F:13])=[C:10]([F:12])[F:11].CC(C)([O-])C.[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[F:13][C:9](=[C:10]([F:12])[F:11])[CH2:8][CH2:7][CH:2]([C:1]#[N:5])[C:3]#[N:4]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
First, 6.98 g of malononitrile, 681 mg of tetrabutylammonium bromide, and 10 g of 4-bromo-1,1,2-trifluoro-1-butene were mixed, and while stirring at 0° C. under an atmosphere of nitrogen, 5.92 g of potassium t-butoxide was slowly added. The mixture was further stirred at room temperature for 12 hours. Then, the reaction mixture was poured into water, followed by extraction with t-butyl methyl ether. The organic layer was washed with water, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.31 g of (3,4,4-trifluoro-3-butenyl)malononitrile (the intermediate (17)).
Workup
- stirringThe mixture was further stirred at room temperature for 12 hours
- extractionfollowed by extraction with t-butyl methyl ether
- washThe organic layer was washed with water
- dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-1771747157584ba589c49561df7e757f
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07402691B2
Reaction notes
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