Ethyl Acetate → 4-[5-(3,5-Dichloro-4-cyano-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid

HRID 1027601Notes

Reaction equation

HRID 1027601 reaction equation
C([O:5][C:6](=[O:33])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:17][C:16]([C:22]3[CH:27]=[C:26]([Cl:28])[C:25]([C:29]#[N:30])=[C:24]([Cl:31])[CH:23]=3)([C:18]([F:21])([F:20])[F:19])[O:15][N:14]=2)=[CH:9][C:8]=1[CH3:32])(C)(C)C.FC(CC(O)=O)(F)F.C(OCC)(=O)C>ClCCl>[Cl:31][C:24]1[CH:23]=[C:22]([C:16]2([C:18]([F:21])([F:19])[F:20])[O:15][N:14]=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([C:6]([OH:33])=[O:5])=[C:8]([CH3:32])[CH:9]=3)[CH2:17]2)[CH:27]=[C:26]([Cl:28])[C:25]=1[C:29]#[N:30]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 27779723,3,3-Trifluoropropionic acidHCID 672466894-[5-(3,5-Dichloro-4-cyano-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid tert-butyl ester

Product 1

HCID 672469284-[5-(3,5-Dichloro-4-cyano-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[5-(3,5-Dichloro-4-cyano-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid tert-butyl ester (763 mg) in dichloromethane (9 ml) was added trifluoromethyl acetic acid (“TFA”) (0.9 ml). The reaction mixture was stirred at ambient temperature for 20 hours. Ethyl acetate was added and the mixture was washed with water, dried over sodium sulfate and concentrated to give 4-[5-(3,5-Dichloro-4-cyano-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid. 19F-NMR (CDCl3, 75 MHz): −78.91 ppm.

Workup

  1. washthe mixture was washed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e2866aadb44e411b901548da0078c375
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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