Potassium vinyltrifluoroborate → HCID 66643943, compound

HRID 1187066Notes

Reaction equation

HRID 1187066 reaction equation
Br[C:2]1[CH:11]=[C:10]([CH3:12])[C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[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]>[CH3:13][C:3]1[C:4]2[CH2:8][O:7][C:6](=[O:9])[C:5]=2[C:10]([CH3:12])=[CH:11][C:2]=1[CH:14]=[CH2:15]

Participants

5

Reactant 2

HCID 23679353Potassium vinyltrifluoroborateHCID 66643951HCID 66643951, compound

Product 1

HCID 66643943HCID 66643943, 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-4,7-dimethyl-2-benzofuran-1(3H)-one (0.7 g, 2.9 mmol), potassium vinyltrifluoroborate (0.544 g, 4 mmol) and Pd(dppf)2Cl2 (0.07 g) in 20 mL of EtOH and 20 mL of TEA was refluxed under N2 for 4 hours. The mixture was concentrated and the residue was purified by column chromatography to afford 4,7-Dimethyl-5-vinyl-2-benzofuran-1(3H)-one. 1H-NMR (400 MHz, CDCl3) δ ppm 7.30 (s, 1H), 6.85-6.92 (m, 1H), 5.70 (d, J=17.3 Hz, 1H), 5.40 (d, J=11.0 Hz, 1H), 5.18 (s, 2H), 2.64 (s, 3H), 2.24 (s, 3H).

Workup

  1. temperaturewas refluxed under N2 for 4 hours
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0782ab2634c64deaa97340270b121ec1
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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