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

HRID 1848523
Notes
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Reaction equation

HRID 1848523 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702Ethanol
Solvent

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. 1H-NMR (400 MHz, CDCl3) δ ppm 7.67-7.68 (m, 2H), 6.90-6.97 (m, 1H), 6.00 (d, J=17.2 Hz, 1H), 5.60 (d, J=11.0 Hz, 1H), 5.35 (s, 2H).

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-fc27557475df4770a555e0f18a477a32
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08952166B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes