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

HRID 1474316Notes

Reaction equation

HRID 1474316 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, 6.008 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. When TLC showed complete reaction 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 4-cyclopropyl-5-vinyl-2-benzofuran-1(3H)-one.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 8 hours
  3. customreaction most of the solvent
  4. customwas 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-a7eb592f04594486b5033f638ffd782e
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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