Potassium vinyltrifluoroborate → HCID 66643955, compound

HRID 2175883Notes

Reaction equation

HRID 2175883 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. 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 the title compound.

Workup

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

Sources & evidence

ORD record
ord-f800465db2d3484b98d4beb6ecd3d706
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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