Acetone → 2-(4-Bromo-3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropanoic acid

HRID 1961691Notes

Reaction equation

HRID 1961691 reaction equation
[OH-:1].[Na+].[Br:3][C:4]1[C:5]([CH3:10])=[N:6][NH:7][C:8]=1[CH3:9].Cl[C:12](Cl)(Cl)[C:13](O)([CH3:15])[CH3:14].CC(C)=[O:21]>>[Br:3][C:4]1[C:5]([CH3:10])=[N:6][N:7]([C:13]([CH3:15])([CH3:14])[C:12]([OH:21])=[O:1])[C:8]=1[CH3:9]

Participants

5

Reactant 4

HCID 180AcetoneHCID 5977ChlorobutanolHCID 14798Sodium HydroxideHCID 769374-bromo-3,5-dimethyl-1H-pyrazole

Product 1

HCID 666281952-(4-Bromo-3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropanoic acid

Procedure

To a cold (0° C.), well stirred suspension of NaOH (1.6 g, 40 mmoles) and 4-bromo-3,5-dimethylpyrazole (1.75 g, 10 mmoles) in acetone (100 mL), was added 2-(trichloromethyl)-propan-2-ol (3.54 g, 20 mmoles) portion-wise over 1 hour. The mixture was allowed to warm to room temperature overnight. The solvent was evaporated under reduced pressure. The residue was dissolved in water (100 mL) and washed with ether (50 mL). The aqueous phase was separated and acidified with conc. HCl to pH=3. The mixture was extracted with CH2Cl2 (3×50 mL) and the combined organics dried over Na2SO4. A colorless oil was obtained after the removal of the solvent under reduced pressure. MS (DCI+) m/z 263 (M+H)+.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in water (100 mL)
  3. washwashed with ether (50 mL)
  4. customThe aqueous phase was separated
  5. extractionThe mixture was extracted with CH2Cl2 (3×50 mL)
  6. dry with materialthe combined organics dried over Na2SO4
  7. customA colorless oil was obtained
  8. customafter the removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-b1d959d5aa1844d7a57539abb281105e
Source dataset
uspto-grants-2013_04
Patent number
US08415354B2

Reaction notes

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