Potassium vinyltrifluoroborate → HCID 66643955, compound

HRID 2281323Notes

Reaction equation

HRID 2281323 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1I.[CH:13]([B-](F)(F)F)=[CH2:14].[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]>[Br:1][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:13]=[CH2:14]

Participants

5

Reactant 2

HCID 23679353Potassium vinyltrifluoroborateHCID 66643942HCID 66643942, compound

Product 1

HCID 66643955HCID 66643955, compound

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-iodo-2-benzofuran-1(3H)-one (1 g, 2.95 mmol), potassium vinyltrifluoroborate (474 mg, 3.54 mmol) and Pd(dppf)Cl2 (200 mg) in 20 mL of TEA and 20 mL of EtOH was heated to reflux under N2 for 2 hours. 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 to provide 5-bromo-4-vinyl-2-benzofuran-1 (3H)-one.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 2 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

Sources & evidence

ORD record
ord-b471e7d2814041ad94445b327906878d
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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