Potassium vinyltrifluoroborate → HCID 66643894, compound

HRID 1501952Notes

Reaction equation

HRID 1501952 reaction equation
[Br:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1Br.[CH:13]([B-](F)(F)F)=[CH2:14].[K+]>CCO.CCOC(C)=O.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[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:13]=[CH2:14]

Participants

6

Reactant 2

HCID 23679353Potassium vinyltrifluoroborateHCID 66819934HCID 66819934, compound

Product 1

HCID 66643894HCID 66643894, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

4,5-Dibromo-2-benzofuran-1(3H)-one (3.00 g, 10.3 mmol), Potassium vinyltrifluoroborate (12.7 g, 20.6 mmol) and Pd(dppf)Cl2 (839 mg, 1.03 mmol) in TEA (2.7 mL) and EtOH (15 mL) were added to a flask containing a stir bar. The flask was then heated at 60° C. for 2 h. TLC showed clean and complete reaction. The organic residue was dissolved in EtOAc (500 mL) and the solution was washed with brine, dried over sodium sulfate, filtered and concentrated. The resulting organic residue was subjected to purification over silica gel to give 4-bromo-5-ethenyl-2-benzofuran-1(3H)-one.

Workup

  1. additioncontaining a stir bar
  2. customcomplete reaction
  3. washthe solution was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting organic residue was subjected to purification over silica gel

Sources & evidence

ORD record
ord-b043cc21a0d742ca871442f860401d14
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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