Potassium Carbonate → 2-Methyl-2-(4-vinylphenyl)propanoic acid

HRID 61871Notes

Reaction equation

HRID 61871 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH:14]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:15]=1.C([B-](F)(F)F)=C.[K+].C(=O)([O-])[O-].[K+].[K+]>C(O)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:14]([C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1)=[CH2:15]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 109336792-(4-Bromophenyl)-2-methylpropanoic acidHCID 23679353Potassium vinyltrifluoroborate

Product 1

HCID 668345512-Methyl-2-(4-vinylphenyl)propanoic acidYield 598.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Procedure

2-(4-Bromophenyl)-2-methylpropanoic acid (30 g), PPh3 (5.0 g), potassium vinyltrifluoroborate (24.8 g), potassium carbonate (51.2 g), and palladium acetate (1.43 g) were dissolved in 1-propanol (198 ml) and distilled water (99 ml). After deaeration, the mixture was stirred under reflux for 6 hrs under nitrogen atmosphere. Insoluble matters were removed by filtration and washed with 1-propanol (210 ml). The filtrate was then concentrated under reduced pressure. Concentrated residues were partitioned between CPME (300 ml) and distilled water (150 ml, comprising 4.17 ml of ethylenediamine) The organic layer was removed and the aqueous layer was adjusted to pH 5 by using 2 N hydrochloric acid. The aqueous layer was extracted with a mixture of isopropyl acetate (240 ml) and heptane (240 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Ethanol (300 ml) was added thereto for suspending and washing the resultant. The solid was removed by Celite filtration, and the filtrate was concentrated under reduced pressure to obtain the title compound (21.7 g, 93%).

Workup

  1. distillationdistilled water (99 ml)
  2. temperatureunder reflux for 6 hrs under nitrogen atmosphere
  3. customInsoluble matters were removed by filtration
  4. washwashed with 1-propanol (210 ml)
  5. concentrationThe filtrate was then concentrated under reduced pressure
  6. customConcentrated residues were partitioned between CPME (300 ml)
  7. distillationdistilled water (150 ml, comprising 4.17 ml of ethylenediamine) The organic layer
  8. customwas removed
  9. extractionThe aqueous layer was extracted with a mixture of isopropyl acetate (240 ml) and heptane (240 ml)
  10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. additionEthanol (300 ml) was added
  13. washwashing the resultant
  14. customThe solid was removed by Celite filtration
  15. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c54bf4c4ceb34b8ca33306f12197988e
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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