(3,4-Difluorophenyl)acetic acid → HCID 53894677, compound

HRID 1899066Notes

Reaction equation

HRID 1899066 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:13][S:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.C[O-].[Na+]>C(OC(=O)C)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:9](=[CH:19][C:18]2[CH:21]=[CH:22][C:15]([S:14][CH3:13])=[CH:16][CH:17]=2)[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 69571(3,4-Difluorophenyl)acetic acidHCID 769854-(Methylthio)benzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 53894677HCID 53894677, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 3,4-difluorophenylacetic acid (10 g), 4-(methylthio)benzaldehyde (8.84 g) and sodium methoxide (3.14 g) in acetic anhydride (30 ml) was refluxed for 20 hours. The solvent was evaporated, and the residue was dissolved in ethyl acetate, washed with dilute hydrochloric acid and water, dried and concentrated to dryness. The obtained solid material was washed with ethanol and dried to give crystals of 2-(3,4-difluorophenyl)-3-[4-(methylthio)phenyl]acrylic acid (12.1 g).

Workup

  1. temperaturewas refluxed for 20 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with dilute hydrochloric acid and water
  5. customdried
  6. concentrationconcentrated to dryness
  7. washThe obtained solid material was washed with ethanol
  8. customdried

Sources & evidence

ORD record
ord-110f2b4faa304f14ac4aa1d1a49c2ff0
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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