Hydrochloric Acid → 4-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(2,2,2-trifluoroethyl)benzoic acid

HRID 63866Notes

Reaction equation

HRID 63866 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([C:33]([F:36])([F:35])[F:34])[O:16][N:15]=[C:14]([C:17]3[CH:27]=[CH:26][C:20]([C:21]([O:23]CC)=[O:22])=[C:19]([CH2:28][C:29]([F:32])([F:31])[F:30])[CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.CO.[OH-].[Na+].Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([C:33]([F:35])([F:34])[F:36])[O:16][N:15]=[C:14]([C:17]3[CH:27]=[CH:26][C:20]([C:21]([OH:23])=[O:22])=[C:19]([CH2:28][C:29]([F:31])([F:32])[F:30])[CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 118046612Ethyl 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(2,2,2-trifluoroethyl)benzoate

Product 1

HCID 1180466734-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(2,2,2-trifluoroethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Into a 50-mL pressure tank reactor (10 atm), was placed ethyl 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(2,2,2-trifluoroethyl)benzoate (300 mg, 0.55 mmol, 1.00 equiv), methanol (5 mL), sodium hydroxide (600 mg, 15.00 mmol, 13.69 equiv), water (5 mL). The resulting solution was stirred overnight at 70° C. The pH value of the solution was adjusted to 5 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 3×10 mL of brine. The mixture was dried over sodium sulfate and concentrated under vacuum. This resulted in 200 mg (crude) of 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(2,2,2-trifluoroethyl)benzoic acid as yellow oil.

Workup

  1. customInto a 50-mL pressure tank reactor (10 atm), was placed
  2. extractionThe resulting solution was extracted with 3×10 ml of ethyl acetate
  3. washThe resulting mixture was washed with 3×10 mL of brine
  4. dry with materialThe mixture was dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 200 mg (crude) of 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(2,2,2-trifluoroethyl)benzoic acid as yellow oil

Sources & evidence

ORD record
ord-6fef201e9bde4dd79ecab12ddda90fb7
Source dataset
uspto-grants-2016_09
Patent number
US09447084B2

Reaction notes

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