Potassium vinyltrifluoroborate → HCID 66643952, compound

HRID 2281325Notes

Reaction equation

HRID 2281325 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[CH2:12][CH3:13].[CH:14]([B-](F)(F)F)=[CH2:15].[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]>[CH2:12]([C:3]1[C:4]2[CH2:8][O:7][C:6](=[O:9])[C:5]=2[CH:10]=[CH:11][C:2]=1[CH:14]=[CH2:15])[CH3:13]

Participants

5

Reactant 2

HCID 23679353Potassium vinyltrifluoroborateHCID 66643986HCID 66643986, compound

Product 1

HCID 66643952HCID 66643952, compound

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-ethyl-2-benzofuran-1(3H)-one (1.81 g, 7.51 mmol), potassium vinyltrifluoroborate (1.21 g, 9.01 mmol) and Pd(dppf)Cl2 (200 mg) in 20 mL of TEA and 20 mL of EtOH was heated to reflux under N2 overnight and then concentrated. The resulting oil was purified by column chromatography to give 4-ethyl-5-vinyl-2-benzofuran-1(3H)-one.

Workup

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

Sources & evidence

ORD record
ord-169f9fe4701c455f9812544a3082c720
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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