Methyl 3-iodobenzoate → Methyl 3-ethylbenzoate

HRID 4974

Reaction equation

HRID 4974 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH:12]([Sn](CCCC)(CCCC)CCCC)=[CH2:13].[F-].[K+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:12]([C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:13]

Participants

8

Reactant 3

HCID 69258Methyl 3-iodobenzoateHCID 81998TributylvinyltinHCID 522689Potassium Fluoride

Product 1

HCID 12430992Methyl 3-ethylbenzoate

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

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.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux
  3. stirringto stir under N2 for 15 minutes
  4. washwashed with water
  5. extractionThe organic extract
  6. dry with materialwas dried (MgSO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-2bbab0f4ae63457f992a8d6c141b0c62
Source dataset
uspto-grants-1993_09
Patent number
US05242930

Linked notes

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