Potassium Carbonate → 1,3-Bis(trifluoromethyl)-5-(1,1,1-trifluoroprop-2-en-2-yl)benzene

To a solution of 20.0 g of 3,5-bis(trifluoromethyl)phenylboronic acid in 100 mL of tetrahydrofuran and 40 mL of water, 20.2 g of 2-bromo-3,3,3-trifluoropropene, 30.0 g of potassium carbonate and 0.023 g of 1,3-bis(2,6-diisopropylphenyl) imidazole-2-ylidene(1,4-naphthoquinone) palladium (0) dimer were added and the resultant mixture was stirred at 60° C. in a nitrogen atmosphere for 3 hours. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature and 100 mL of ice water was added to the reaction mixture, followed by extracting the resultant mixture with ethyl acetate (100 mL×2). The organic phase was washed with water and then dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with hexane to obtain 21.9 g of the objective substance as an orange oily substance.

1. customAfter the completion of the reaction
2. waitthe reaction mixture was left
3. extractionby extracting the resultant mixture with ethyl acetate (100 mL×2)
4. washThe organic phase was washed with water
5. dry with materialdried over saturated saline and anhydrous sodium sulfate in this order
6. distillationthe solvent was distilled off under reduced pressure
7. customThe resultant residue was purified by silica gel column chromatography
8. washeluting with hexane
9. customto obtain 21.9 g of the objective substance as an orange oily substance

ORD record

ord-72fa108577b04b73a871021f3438b344

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318757B2