3-(2-Fluorophenyl)prop-2-enoic acid → Methyl 3-(2-fluorophenyl)propanoate

HRID 1872092Notes

Reaction equation

HRID 1872092 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7].[H][H].CO.[C:17](OCC)(=O)C>[Pd]>[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH2:4][CH2:5][C:6]([O:8][CH3:17])=[O:7]

Participants

5

Reactant 3

HCID 679773-(2-Fluorophenyl)prop-2-enoic acidHCID 21584119Ethylacetate methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 15479441Methyl 3-(2-fluorophenyl)propanoate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a Parr vessel is placed 2-fluorocinnamic acid (1h) (1.0 equiv) and palladium on carbon in a 1/1 methanol/ethyl acetate solution. The heterogeneous solution is placed on a Parr shaker and treated with hydrogen (50 psi) until uptake has ceased. The mixture is filtered through Celite and concentrated under reduced pressure. The residue is taken up in diethyl ether and treated with diazomethane until a yellow color persists. The solution is concentrated under reduced pressure to give the crude methyl ester. Purification is effected by column chromatography on silica gel (hexane/ethyl acetate 5/1) to yield Methyl 3-(2-fluorophenyl)propionate (1i) in quantitative yield.

Workup

  1. filtrationThe mixture is filtered through Celite
  2. concentrationconcentrated under reduced pressure
  3. additiontreated with diazomethane until a yellow color persists
  4. concentrationThe solution is concentrated under reduced pressure
  5. customto give the crude methyl ester
  6. customPurification

Sources & evidence

ORD record
ord-effd9c0d02f74c0fa8788eec2f3dda17
Source dataset
uspto-grants-2000_08
Patent number
US06107338

Reaction notes

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