Sodium Hydroxide → 98534-79-3

HRID 1750395Notes

Reaction equation

HRID 1750395 reaction equation
[Br:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[C:11]([O:13]CC)=[O:12].[OH-].[Na+]>C(O)C.C1COCC1>[Br:1][C:2]1[N:6]([C:7]([CH3:8])([CH3:9])[CH3:10])[N:5]=[CH:4][C:3]=1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53429364Ethyl 5-bromo-1-tert-butyl-1H-pyrazole-4-carboxylate

Product 1

HCID 8613611098534-79-3Yield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixed solution of the compound (13.5 g, 49.07 mmol) obtained in step 2 and 1N aqueous sodium hydroxide solution (65 mL, 65.00 mmol) in ethanol (70 mL) and THF (70 mL) was stirred at 60° C. for 2.5 hr. The organic solvent was evaporated under reduced pressure, and water and 1N hydrochloric acid (70 mL) were added thereto. The precipitate was collected by filtration, and washed with diethyl ether and hexane to give 5-bromo-1-tert-butyl-1H-pyrazole-4-carboxylic acid (10.29 g, 41.6 mmol, 85%) as a white powder.

Workup

  1. customThe organic solvent was evaporated under reduced pressure, and water and 1N hydrochloric acid (70 mL)
  2. additionwere added
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with diethyl ether and hexane

Sources & evidence

ORD record
ord-4b4d8d18a2cf4c4f98ea3d4c1637599e
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

Loading…