Trifluoroacetic acid → [3-Chloro-4-(trifluoromethyl)phenoxy]acetic acid

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[C:17]([F:20])([F:19])[F:18])[O:5][CH2:6][C:7]([O:9]C(C)(C)C)=[O:8].FC(F)(F)C(O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[C:17]([F:18])([F:19])[F:20])[O:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 58640420tert-Butyl [3-chloro-4-(trifluoromethyl)phenoxy]acetate

Product 1

HCID 21097484[3-Chloro-4-(trifluoromethyl)phenoxy]acetic acidYield 80%

Procedure

tert-Butyl [3-chloro-4-(trifluoromethyl)phenoxy]acetate (1.2 g, 3.8 mmol) was added trifluoroacetic acid (TFA) (3 ml). The mixture was stirred for 5 hours at ambient temperature. The solvent was removed under reduced pressure to give the residue, which was applied to a recrystallization from hexane-methylene dichloride to furnish 251 mg (80% yield) of the title compound as a brown solid.

Workup

customThe solvent was removed under reduced pressure
customto give the residue, which
customwas applied to a recrystallization from hexane-methylene dichloride

Sources & evidence

ORD record: ord-3354943425a34c6ea8199794d0bb8eb7
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214824B2

Reaction notes

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