Trifluoroacetic acid → 2-(3,5-Difluoro-4-nitrophenyl)acetic acid

HRID 1622961Notes

Reaction equation

HRID 1622961 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([O:15]C(C)(C)C)=[O:14])[CH:5]=[C:6]([F:11])[C:7]=1[N+:8]([O-:10])=[O:9].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[C:6]([F:11])[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18188101t-Butyl 3,5-difluoro4-nitrophenylacetate

Product 1

HCID 179671372-(3,5-Difluoro-4-nitrophenyl)acetic acidYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (3,5-difluoro-4-nitrophenyl)acetate (4.34 g, 15.88 mmol) in DCM (10 ml), at 0° C., was added TFA (10 ml). The reaction was warmed to room temperature and stirred for 1.5 hours. The reaction was concentrated in vacuo, slurried in heptane (10 ml), filtered and dried to provide the title compound as an orange solid (2.95 g, 86% yield).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-9a35f1a3c6c845ec833c3c6ad9cebe87
Source dataset
uspto-grants-2014_07
Patent number
US08778953B2

Reaction notes

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