Reacción #5070

ord-2bbab0f4ae63457f992a8d6c141b0c62

Ecuación de reacción

[F-].[K+]
Potassium fluoride
COC(=O)c1cccc(I)c1
Methyl 3-iodobenzoate
C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC
vinyl tributyltin
→
CCc1cccc(C(=O)OC)c1
Methyl 3-ethylbenzoate

Reactantes

[F-].[K+]
Potassium fluoride
COC(=O)c1cccc(I)c1
Methyl 3-iodobenzoate
C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC
vinyl tributyltin

Reactivos

c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
tetrakis(triphenylphosphine)palladium

Disolventes

O
water
Cc1ccccc1
toluene
CCOC(C)=O
ethyl acetate

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe solution was heated
  2. 2
    Temperaturaat reflux
  3. 3
    workup.STIRRINGto stir under N2 for 15 minutes
  4. 4
    Lavadowashed with water
  5. 5
    ExtracciónThe organic extract
  6. 6
    Secadowas dried (MgSO4)
  7. 7
    Otroevaporated in vacuo

Procedimiento

Methyl 3-iodobenzoate (13 g) and vinyl tributyltin (20 g) were dissolved in toluene (100 ml) and tetrakis(triphenylphosphine)palladium (0) (500 mg) added. The solution was heated at reflux with stirring under N2 for 1 day. Potassium fluoride (3 g) in water (50 ml) was added and the reaction mixture was allowed to stir under N2 for 15 minutes. The product was taken up in ethyl acetate and washed with water and then brine (×2). The organic extract was dried (MgSO4) and evaporated in vacuo.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05242930uspto-grants-1993_09