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

HRID 1510438Notes

Reaction equation

HRID 1510438 reaction equation
O.[OH-].[Li+].[Cl:4][C:5]1[C:6]([C:20]([O:22]CC)=[O:21])=[N:7][O:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1.Cl>O.O1CCCC1.ClCCl>[Cl:4][C:5]1[C:6]([C:20]([OH:22])=[O:21])=[N:7][O:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:19])[F:18])=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67121079Ethyl 4-chloro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylate

Product 1

HCID 671210774-Chloro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylic acidYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide hydrate (126 mg, 3.0 mmol) in water (18 mL) was added to a solution of ethyl 4-chloro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylate (0.96 g, 3.0 mmol) in tetrahydrofuran (15 mL). After stirring for 45 minutes, the reaction mixture was diluted with dichloromethane (30 mL), and the aqueous layer was adjusted to pH=2 with 6N aqueous HCl. The resulting mixture was extracted 3 times with dichloromethane, the dichloromethane layers were combined, dried over Na2SO4, and concentrated in vacuo to obtain the title compound (0.88 g, 3.0 mmol).

Workup

  1. extractionThe resulting mixture was extracted 3 times with dichloromethane
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d981ad6c6464a53969fc7b187de09d6
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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