Potassium vinyltrifluoroborate → 4-fluoro-5-vinyl-3H-isobenzofuran-1-one

HRID 1474327Notes

Reaction equation

HRID 1474327 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[F:12].[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:3]1[C:2]([CH:13]=[CH2:14])=[CH:11][CH:10]=[C:5]2[C:4]=1[CH2:8][O:7][C:6]2=[O:9]

Participants

5

Reactant 2

HCID 23679353Potassium vinyltrifluoroborateHCID 666440385-Bromo-4-fluoro-1,3-dihydro-2-benzofuran-1-one

Product 1

HCID 666441764-fluoro-5-vinyl-3H-isobenzofuran-1-one

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-fluoro-2-benzofuran-1(3H)-one (5.0 g, 21.6 mmol), potassium vinyltrifluoroborate (4.4 g, 32.5 mmol) and Pd(dppf)Cl2 (500 mg) in 100 mL of TEA and 100 mL of EtOH was heated to reflux under N2 for 4 hrs and then concentrated. The resulting oil was purified by column chromatography to give 4-fluoro-5-vinyl-3H-isobenzofuran-1-one.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 4 hrs
  3. concentrationconcentrated
  4. customThe resulting oil was purified by column chromatography

Sources & evidence

ORD record
ord-a679e2bcaeed44bb865cedd65a3ec7a6
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

Loading…