Trifluoroacetic acid → 2-(4-Fluoro-2-methylphenyl)acetic acid

HRID 1993981Notes

Reaction equation

HRID 1993981 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11]C(C)(C)C)=[O:10])=[C:4]([CH3:16])[CH:3]=1.C(C(O)=O)(F)(F)F>C(Cl)Cl.C1(OC)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([CH3:16])[CH:3]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86620047Tert-butyl (4-fluoro-2-methylphenyl)acetate

Product 1

HCID 50169502-(4-Fluoro-2-methylphenyl)acetic acid

Reagents, catalysts & solvents 2

HCID 7519AnisoleCatalystHCID 6344DichloromethaneSolvent

Procedure

The pure ester was dissolved in 60 ml of CH2Cl2 was added 6 drops of anisole and 60 ml of CF3CO2H and the solution was atirred at rt for 16 hr. Upon removal of volatiles, the residue was dried three times by dissolving in toluene to afford 20.02 g of the title compound. 1H-NMR (CDCl3): δ 2.35 (s, 3H), 3.67 (s, 2H), 6.92-6.95 (m, 2H), 7.19 (d of d, 1H, J=8.2, 5.7 Hz) ppm.

Workup

  1. customUpon removal of volatiles
  2. customthe residue was dried three times
  3. dissolutionby dissolving in toluene

Sources & evidence

ORD record
ord-0c524a293baa4cde985fe3030bad9514
Source dataset
uspto-grants-2010_01
Patent number
US07652058B2

Reaction notes

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