Potassium vinyltrifluoroborate → HCID 66643894, compound

HRID 1474199Notes

Reaction equation

HRID 1474199 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

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 heated at 60° C. for 2 h. Analysis by TLC showed clean and complete reaction. The reaction mixture was diluted with EtOAc (500 mL), washed with brine, dried over sodium sulfate, filtered, and concentrated. The resulting residue was subjected to purification over silica gel to give 4-bromo-5-ethenyl-2-benzofuran-1(3H)-one.

Workup

  1. customcomplete reaction
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was subjected to purification over silica gel

Sources & evidence

ORD record
ord-56222a994dfc4ab9b008374e47c63b2c
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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