Hydrochloric Acid → 5-[2-(Trifluoromethyl)phenyl]-1,2-oxazole-4-carboxylic acid

HRID 474359Notes

Reaction equation

HRID 474359 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][O:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([F:20])([F:19])[F:18])=[O:5])C.Cl>C(O)(=O)C>[F:19][C:17]([F:18])([F:20])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]1[O:9][N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20297498Ethyl 5-(2-(trifluoromethyl)phenyl)isoxazole-4-carboxylate

Product 1

HCID 591702015-[2-(Trifluoromethyl)phenyl]-1,2-oxazole-4-carboxylic acidYield 58%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5-(2-trifluoromethyl-phenyl)-isoxazole-4-carboxylic acid ethyl ester (1.43 g, 5.01 mmol, 1.0 equiv), 6M HCl aqueous solution (34 mL) and acetic acid (20 mL) were heated to reflux for 5.5 hours. After cooling, the mixture was partitioned between water and ethyl acetate and separated. The organic phase was washed sequentially with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under vacuum to give 745 mg (58%) of crude 5-(2-trifluoromethyl-phenyl)-isoxazole-4-carboxylic acid which was used without purification.

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 5.5 hours
  3. temperatureAfter cooling
  4. customthe mixture was partitioned between water and ethyl acetate
  5. customseparated
  6. washThe organic phase was washed sequentially with water and saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ee3f5352a00244478d524148f0ca602a
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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