Potassium Carbonate → HCID 59378906, compound

HRID 1027599Notes

Reaction equation

HRID 1027599 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1.Br[C:16]([C:18]([F:21])([F:20])[F:19])=[CH2:17].C(=O)([O-])[O-].[K+].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.O>[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:16]([C:18]([F:21])([F:20])[F:19])=[CH2:17])[CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2726961-Propene, 2-bromo-3,3,3-trifluoro-HCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 59378906HCID 59378906, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-Trifluoromethoxy-benzeneboronic acid (2.5 g) in a 2:1 mixture THF/H2O (36 ml) was added 2-Bromo-3,3,3-trifluoro-propene (3.1 ml), potassium carbonate (3.35 g), then Bis(triphenylphosphine)palladium(II) dichloride (169 mg). The reaction mixture was stirred at 60° C. for 7 hours. The solution was allowed to cool to room temperature then filtered on a Celite pad. The filtrate was concentrated in vacuo and the residue was then dissolved with ethyl acetate, extracted with water, dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel to give 1-Trifluoromethoxy-3-(1-trifluoromethyl-vinyl)-benzene (1.23 g). 19F-NMR (CDCl3, 75 MHz): −57.87 ppm and −64.94 ppm.

Workup

  1. temperatureto cool to room temperature
  2. filtrationthen filtered on a Celite pad
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionthe residue was then dissolved with ethyl acetate
  5. extractionextracted with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-09ff8aca0cbf417ea46c210f16230496
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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