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

HRID 1187073Notes

Reaction equation

HRID 1187073 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>[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

4

Reactant 2

HCID 23679353Potassium vinyltrifluoroborateHCID 66643914HCID 66643914, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 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. 1H-NMR (400 MHz, CDCl3) δ ppm 7.23 (s, 1H), 7.17 (d, J=10.0 Hz, 1H), 6.70-6.77 (m, 1H), 5.89 (d, J=17.2 Hz, 1H), 5.51 (d, J=11.2 Hz, 1H), 5.28 (s, 2H).

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-ba628d8160eb49ea83462ab58f1602e0
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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