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

HRID 885821Notes

Reaction equation

HRID 885821 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5](OB(O)O)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Br[C:20]([C:22]([F:25])([F:24])[F:23])=[CH2:21].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O.CC(C1C=CC=C(C(C)C)C=1N1C(=[Pd])N(C2C(C(C)C)=CC=CC=2C(C)C)C=C1)C.CC(C1C=CC=C(C(C)C)C=1N1C(=[Pd])N(C2C(C(C)C)=CC=CC=2C(C)C)C=C1)C.C1C=C2C(C(C=CC2=O)=O)=CC=1.C1C=C2C(C(C=CC2=O)=O)=CC=1>[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([C:20]([C:22]([F:25])([F:24])[F:23])=[CH2:21])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2726961-Propene, 2-bromo-3,3,3-trifluoro-HCID 177934113,5-Bis(trifluoromethyl)phenyl boric acid

Product 1

HCID 498208821,3-Bis(trifluoromethyl)-5-(1,1,1-trifluoroprop-2-en-2-yl)benzeneYield 97.3%

Reagents, catalysts & solvents 3

HCID 111824871,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene(1,4-naphthoquinone)palladium(0) dimerCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 3,5-bis(trifluoromethyl)phenyl boric acid (20.0 g) in tetrahydrofuran (100 mL) and water (40 mL) was added 2-bromo-3,3,3-trifluoropropene (20.2 g) and potassium carbonate (30.0 g), followed by the addition of 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene(1,4-naphthoquinone)palladium(0) dimer (0.023 g). The reaction mixture was stirred at 60° C. for 3 hours under nitrogen atmosphere and then cooled to room temperature. The resulting mixture was poured into ice-water (100 mL) and extracted with ethyl acetate (100 mL×2). The organic extracts were combined, washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide a residue. The residue was purified by column chromatography on silica gel eluted with hexane to afford the title compound as orange oil (21.9 g).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate (100 mL×2)
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto provide a residue
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluted with hexane

Sources & evidence

ORD record
ord-009cf12088e94930a095d86288077e0d
Source dataset
uspto-grants-2012_08
Patent number
US08242283B2

Reaction notes

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