Malononitrile → (3,4,4-Trifluoro-3-butenyl)malononitrile

Participants

Reaction Conditions

Reaction Steps

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)).

Provenance & Evidence