Hydrochloric Acid → 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-trifluoromethyl benzoic acid

HRID 467941Notes

Reaction equation

HRID 467941 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:14][C:13]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)([C:15]([F:18])([F:17])[F:16])[O:12][N:11]=2)=[CH:6][C:5]=1[C:27]([F:30])([F:29])[F:28].[OH-].[K+].Cl>O1CCCC1.CO.O>[Cl:26][C:21]1[CH:20]=[C:19]([C:13]2([C:15]([F:17])([F:16])[F:18])[O:12][N:11]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:31])=[O:2])=[C:5]([C:27]([F:30])([F:28])[F:29])[CH:6]=3)[CH2:14]2)[CH:24]=[C:23]([Cl:25])[CH:22]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 595634864-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-trifluoromethyl benzoic acid methyl ester

Product 1

HCID 595634844-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-trifluoromethyl benzoic acidYield 85.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-trifluoromethyl-benzoic acid methyl ester (Example I13) (4.3 g) in tetrahydrofuran (3 ml) and methanol (3 ml) was added a solution of potassium hydroxide (1.0 g) in water (4.0 ml). The reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was acidified by addition of hydrochloric acid (2M) (200 ml) and the mixture extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated. The residue was re-crystallized from dichloromethane and heptane to give 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-trifluoromethyl-benzoic acid (3.58 g) as a white powder. 1H-NMR (CDCl3, 400 MHz): 8.08-7.45 (m, 6H), 4.14 (d, 1H), 3.76 (d, 1H).

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×100 ml)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was re-crystallized from dichloromethane and heptane

Sources & evidence

ORD record
ord-51171e0c96694077967b519be0cebbcb
Source dataset
uspto-grants-2014_01
Patent number
US08623896B2

Reaction notes

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