Sodium Hydroxide → 4-(5-(3,5-Dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid

HRID 63879Notes

Reaction equation

HRID 63879 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:26]([F:29])([F:28])[F:27])[O:14][N:13]=[C:12]([C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[C:17]([CH3:25])[CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:26]([F:28])([F:29])[F:27])[O:14][N:13]=[C:12]([C:15]3[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[C:17]([CH3:25])[CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118046800HCID 118046800, compound

Product 1

HCID 866854534-(5-(3,5-Dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Into a 50-mL round-bottom flask, was placed methanol (5 mL), methyl 4-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoate (60 mg, 0.13 mmol, 1.00 equiv), 15% NaOH (2 mL). The resulting solution was stirred for 2 h at 60° C. in an oil bath. The reaction mixture was cooled. The resulting mixture was concentrated under vacuum. The pH value of the solution was adjusted to 3-4 with hydrogen chloride (3 mol/L). The resulting solution was extracted with 3×10 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×5 mL of Brine. The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 57 mg (98%) of 4-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoic acid as a white solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. temperatureThe reaction mixture was cooled
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. extractionThe resulting solution was extracted with 3×10 mL of ethyl acetate
  5. washThe resulting mixture was washed with 3×5 mL of Brine
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThis resulted in 57 mg (98%) of 4-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoic acid as a white solid

Sources & evidence

ORD record
ord-2fac527f8ef14c6a89eb26fb2f5daf1c
Source dataset
uspto-grants-2016_09
Patent number
US09447084B2

Reaction notes

Loading…