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

HRID 1474261Notes

Reaction equation

HRID 1474261 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-4acc222f44414dca89c528f94dabedda
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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