Reaction #5070

ord-2bbab0f4ae63457f992a8d6c141b0c62

Reaction equation

[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

Reactants

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

Reagents

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

Solvents

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

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe solution was heated
  2. 2
    Temperatureat reflux
  3. 3
    workup.STIRRINGto stir under N2 for 15 minutes
  4. 4
    Washwashed with water
  5. 5
    ExtractionThe organic extract
  6. 6
    Dryingwas dried (MgSO4)
  7. 7
    Otherevaporated in vacuo

Procedure

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05242930uspto-grants-1993_09