Hydrochloric Acid → 4-Fluoro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylic acid

HRID 1510442Notes

Reaction equation

HRID 1510442 reaction equation
[F:1][C:2]1[C:3]([C:17]([O:19]CC)=[O:18])=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.[OH-].[Li+].Cl>O1CCCC1.O>[F:1][C:2]1[C:3]([C:17]([OH:19])=[O:18])=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:14])([F:16])[F:15])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67121190Ethyl 4-fluoro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylate

Product 1

HCID 671210674-Fluoro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylic acidYield 97.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-fluoro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylate (147 mg, 0.48 mmol) in tetrahydrofuran (2.5 mL) was added a solution of lithium hydroxide (20 mg, 0.83 mmol) in water (2.5 mL). After stirring for one hour, the reaction mixture was acidified to pH=2 with 1M HCl, and extracted three times with dichloromethane. The dichloromethane extracts were combined, dried over sodium sulfate and rotoevaporated to obtain the title compound (130 mg, 0.47 mmol).

Workup

  1. extractionextracted three times with dichloromethane
  2. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-e2d73b6f257d432f983e3bda83e87ae3
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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