HCID 86608725, compound → 3-Cyano-4-fluorobenzenepropanoic acid

HRID 2374732Notes

Reaction equation

HRID 2374732 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](/[CH:10]=[CH:11]/[C:12]([O:14]CC2C=CC=CC=2)=[O:13])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]>ClCCl.C(O)C.[Pd]>[C:1]([C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

Participants

4

Reactant 1

HCID 86608725HCID 86608725, compound

Product 1

HCID 691581763-Cyano-4-fluorobenzenepropanoic acidYield 101.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584144Dichloromethane ethanolSolvent

Procedure

Benzyl (E)-3-(3-cyano-4-fluorophenyl)-acrylate (Int. A6) (1.72 g, 6.1 mmol) was dissolved in 1:1 dichloromethane/ethanol (50 ml) and 10% palladium on charcoal (0.5 g) added. The mixture was hydrogenated for 2 h at ambient pressure, filtered and concentrated to provide the title compound as a white solid (1.2 g, 100%). 1H-NMR (CDCl3) δ 2.69 (2H, t), 2.97 (2H, t), 7.11 (1H, m), 7.43 (3H, m).

Workup

  1. additionadded
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-67f0130a1f2b4cbc9c8fbee1ec0b7d52
Source dataset
uspto-grants-2008_12
Patent number
US07462620B2

Reaction notes

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