2-(2-Fluoro-4-biphenylyl)acrylic acid → Flurbiprofen

HRID 1449047Notes

Reaction equation

HRID 1449047 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8](=[CH2:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C.[Pt]>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 205597882-(2-Fluoro-4-biphenylyl)acrylic acid

Product 1

HCID 3394Flurbiprofen

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

The product of Example 2 (0.5 g.) was hydrogenated in ethanol (10 ml.) at room temperature and atmospheric pressure using a platinum catalyst (5 mg.). After 41/2 hours the mixture was filtered and the filtrate concentrated. The product was recrystallised from a mixture of ether and light petroleum (b.p. 40°-60° C.) to give 2-(2-fluoro-4-biphenylyl)propionic acid, m.p. 112°-113° C.

Workup

  1. filtrationAfter 41/2 hours the mixture was filtered
  2. concentrationthe filtrate concentrated
  3. customThe product was recrystallised from a mixture of ether and light petroleum (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-4c6bc32ca00746e7828286d10254664b
Source dataset
uspto-grants-1980_02
Patent number
US04188491

Reaction notes

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