Potassium vinyltrifluoroborate → 4-cyclopropyl-5-vinyl-2-benzofuran-1(3H)-one

HRID 1501829Notes

Reaction equation

HRID 1501829 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[CH:12]1[CH2:14][CH2:13]1.[CH:15]([B-](F)(F)F)=[CH2:16].[K+]>CCO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:12]1([C:3]2[C:4]3[CH2:8][O:7][C:6](=[O:9])[C:5]=3[CH:10]=[CH:11][C:2]=2[CH:15]=[CH2:16])[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 23679353Potassium vinyltrifluoroborateHCID 666439405-Bromo-4-cyclopropyl-1(3H)-isobenzofuranone

Product 1

HCID 666439474-cyclopropyl-5-vinyl-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-bromo-4-cyclopropyl-2-benzofuran-1(3H)-one (760 mg, 3.004 mmol), potassium vinyltrifluoroborate (805 mg, 6.01 mmol) and Pd(dppf)Cl2 (100 mg) in 20 mL of TEA and 20 mL of EtOH was heated to reflux under N2 for 8 hours. After TLC showed complete reaction, then most of the solvent was removed and the residue was dissolved in EtOAc (100 mL). The solution was washed with 0.1 N HCl, sodium bicarbonate, and brine, dried over sodium sulfate, filtered and concentrated. The resulting oil was purified by column chromatography to give the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 8 hours
  3. customreaction
  4. custommost of the solvent was removed
  5. dissolutionthe residue was dissolved in EtOAc (100 mL)
  6. washThe solution was washed with 0.1 N HCl, sodium bicarbonate, and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting oil was purified by column chromatography

Sources & evidence

ORD record
ord-3c297d43fed6424fb20b89abf396c9d9
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

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