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

HRID 2188362Notes

Reaction equation

HRID 2188362 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® hydrogenation 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 is treated with diazomethane until the yellow color persists. The solution is concentrated under reduced pressure giving 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. additionis treated with diazomethane until the yellow color persists
  4. concentrationThe solution is concentrated under reduced pressure
  5. customgiving the crude methyl ester
  6. customPurification

Sources & evidence

ORD record
ord-dbd787ff14394d1695cd6a6b32c936ca
Source dataset
uspto-grants-2002_06
Patent number
US06410780B1

Reaction notes

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