Potassium vinyltrifluoroborate → 5-Ethenyl-7-fluoro-1(3H)-isobenzofuranone

HRID 1474331Notes

Reaction equation

HRID 1474331 reaction equation
Br[C:2]1[CH:11]=[C:10]([F:12])[C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1.[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]>[F:12][C:10]1[C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=[C:2]([CH:13]=[CH2:14])[CH:11]=1

Participants

5

Reactant 2

HCID 23679353Potassium vinyltrifluoroborateHCID 66643914HCID 66643914, compound

Product 1

HCID 666439945-Ethenyl-7-fluoro-1(3H)-isobenzofuranone

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-7-fluoro-2-benzofuran-1(3H)-one (4.6 g, 20.0 mmol), potassium vinyltrifluoroborate (2.9 g, 22 mmol) and Pd(dppf)2Cl2 (0.5 g) in 40 mL of EtOH and 40 mL of TEA was refluxed under Ar for 4 hours. After concentration, the residue was purified by column chromatography (PE:EtOAc=20:1) to afford 7-fluoro-5-vinyl-2-benzofuran-1(3H)-one.

Workup

  1. temperaturewas refluxed under Ar for 4 hours
  2. concentrationAfter concentration
  3. customthe residue was purified by column chromatography (PE:EtOAc=20:1)

Sources & evidence

ORD record
ord-839f039506c94586987c4338d5f9ece9
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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