Ethanol → 4-Ethenyl-3-methyl-2-(methyloxy)benzonitrile

HRID 1187003Notes

Reaction equation

HRID 1187003 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[C:3]=1[CH3:12].[CH3:13][CH2:14]O>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]>[CH:13]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[C:3]=1[CH3:12])=[CH2:14]

Participants

4

Reactant 2

HCID 702EthanolHCID 666438674-Bromo-2-methoxy-3-methylbenzonitrile

Product 1

HCID 666472914-Ethenyl-3-methyl-2-(methyloxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

The mixture of 4-bromo-3-methyl-2-(methyloxy)benzonitrile (8.10 g, 35.8 mmol), potassium vinyl trifluoroborate (6.24 g, 46.6 mmol) and PdCl2(dppf)2 (0.55 g, 0.70 mmol) in 160 mL of EtOH and 40 mL of TEA was refluxed under Ar for 4 hours. The mixture was concentrated, and the residue was purified by column chromatography (PE:EtOAc=20:1) to afford 4-ethenyl-3-methyl-2-(methyloxy)benzonitrile.

Workup

  1. temperaturewas refluxed under Ar for 4 hours
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by column chromatography (PE:EtOAc=20:1)

Sources & evidence

ORD record
ord-f2a68ee9c7b74697b7452c41bcd00d62
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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