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

HRID 2276950Notes

Reaction equation

HRID 2276950 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-a205c55d575d40d2a6a3a4537aff6599
Source dataset
uspto-grants-2015_09
Patent number
US09133145B2

Reaction notes

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