Trifluoroacetic acid → 2-((5-(4-(Trifluoromethoxy)phenyl)benzo[d]isoxazol-3-yl)oxy)acetic acid

HRID 1482871Notes

Reaction equation

HRID 1482871 reaction equation
[F:1][C:2]([F:29])([F:28])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][N:16]=[C:15]([O:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[C:14]=3[CH:27]=2)=[CH:6][CH:5]=1.FC(F)(F)C(O)=O>ClCCl>[F:29][C:2]([F:1])([F:28])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][N:16]=[C:15]([O:18][CH2:19][C:20]([OH:22])=[O:21])[C:14]=3[CH:27]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118161964Tert-butyl 2-((5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazol-3-yl)oxy)acetate

Product 1

HCID 1181618652-((5-(4-(Trifluoromethoxy)phenyl)benzo[d]isoxazol-3-yl)oxy)acetic acidYield 64.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 2-((5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazol-3-yl)oxy)acetate (285 mg, 0.70 mmol) was dissolved in 5 mL dichloromethane. 2 mL trifluoroacetic acid was added and the mixture was stirred at ambient temperature for 3 hours. Volatiles were evaporated under vacuum and the residue was crystallized from ethyl acetate/hexane to give 2-((5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazol-3-yl)oxy)acetic acid (160 mg, 0.453 mmol).

Workup

  1. customVolatiles were evaporated under vacuum
  2. customthe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-672a2b88ed884634a4f3ec61b10f7546
Source dataset
uspto-grants-2016_08
Patent number
US09416115B2

Reaction notes

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