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

HRID 1505273Notes

Reaction equation

HRID 1505273 reaction equation
C([O:5][C:6](=[O:32])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:17]([OH:18])[C:16]([C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=3)([C:19]([F:22])([F:21])[F:20])[O:15][N:14]=2)=[CH:9][C:8]=1[CH3:31])(C)(C)C.FC(F)(F)C(O)=O>ClCCl.O>[Cl:30][C:25]1[CH:24]=[C:23]([C:16]2([C:19]([F:21])([F:20])[F:22])[O:15][N:14]=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([C:6]([OH:32])=[O:5])=[C:8]([CH3:31])[CH:9]=3)[CH:17]2[OH:18])[CH:28]=[C:27]([Cl:29])[CH:26]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 583386234-[5-(3,5-Dichloro-phenyl)-4-hydroxy-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid tert-butyl ester

Product 1

HCID 584979244-[5-(3,5-Dichloro-phenyl)-4-hydroxy-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acidYield 89.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[5-(3,5-dichloro-phenyl)-4-hydroxy-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid tert-butyl ester (Example 12.1) (500 mg) in dichloromethane (20 ml) was added trifluoroacetic acid (“TFA”) (4 ml) and the reaction mixture was stirred at ambient temperature for 16 hours. To the reaction mixture was diluted with water and the phases were separated. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was suspended in diisopropyl ether/pentane (1:3). The solids were isolated by filtration and washed with pentane to give 4-[5-(3,5-dichloro-phenyl)-4-hydroxy-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid (395 mg) as a white solid. M.p. 215-217° C. 1H-NMR (CDCl3, 400 MHz): 7.98 (d, 1H), 7.72 (s, 1H), 7.69 (s, 1H), 7.52 (s, 2H), 7.40 (s, 1H), 5.76 (s, 1H), 2.61 (s, 3H).

Workup

  1. customthe phases were separated
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe solids were isolated by filtration
  6. washwashed with pentane

Sources & evidence

ORD record
ord-356e9876ee0148269509862264070953
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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