Hydrochloric Acid → (4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid

HRID 710615Notes

Reaction equation

HRID 710615 reaction equation
[Cl:1][C:2]1[C:3]([C:14]([F:17])([F:16])[F:15])=[N:4][N:5]([CH2:8][C:9]([O:11]CC)=[O:10])[C:6]=1[CH3:7].O[Li].O.Cl>C1COCC1.O>[Cl:1][C:2]1[C:3]([C:14]([F:16])([F:15])[F:17])=[N:4][N:5]([CH2:8][C:9]([OH:11])=[O:10])[C:6]=1[CH3:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 757300HCID 757300, compound

Product 1

HCID 1876853(4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acidYield 89.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate (7.5 g, 27.7 mmol) in THF (100 mL) and water (50 mL) was added LiOH.H2O (2.33 g, 55.4 mmol). The mixture was stirred at 60° C. for 5 hours. After cooling to room temperature, the mixture was acidified with 1 N HCl (80 mL) and extracted with 1:2 IPA/CHCl3 (2×150 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to give the desired compound (6 g, 24.7 mmol, 89%). 1H NMR (400 MHz, DMSO-d6) δ 4.98 (s, 2H), 2.21 (s, 3H); MS: (ES) m/z calculated for C7H6ClF3N2O2 [M+H]+ 243.0, found 243.0.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with 1:2 IPA/CHCl3 (2×150 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7419d9b7cf04498b8da492d94fcfed2d
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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