3-(2,4-Difluorophenyl)acrylic Acid → 3-(2,4-difluorophenyl)propanoic Acid

HRID 130606

Reaction equation

HRID 130606 reaction equation
[F:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7].[H][H]>[Pd]>[F:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[CH2:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 6035023-(2,4-Difluorophenyl)acrylic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 49863953-(2,4-difluorophenyl)propanoic AcidYield 90%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
100 °C

Procedure

The procedure was as in Example 5, but the 2,4-difluorocinnamic acid obtained was not isolated. The aqueous-acidic product suspension obtained was treated with 2 g of Pd/C (5% strength) at 50° C. with further stirring and heated to 100° C. It was then pressurized to 5 bar of hydrogen. After constant pressure had been achieved, it was cooled to room temperature, the pressure was released and the solid was filtered off. The filter cake was taken up in methylene chloride, the palladium catalyst was filtered off and the solvent was removed. After drying in vacuo, 100.5 g of 3-(2,4-difluorophenyl)propionic acid (90% of theory; melting point: 100° C.) were obtained.

Workup

  1. customwas not isolated
  2. customThe aqueous-acidic product suspension obtained
  3. temperatureit was cooled to room temperature
  4. filtrationthe solid was filtered off
  5. filtrationthe palladium catalyst was filtered off
  6. customthe solvent was removed
  7. customAfter drying in vacuo

Sources & evidence

ORD record
ord-668b816b464443888318838bbd96957b
Source dataset
uspto-grants-2008_06
Patent number
US07381832B2

Linked notes

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