Methanol → methyl 2-(4-bromo-1H-pyrazol-1-yl)propanoate

HRID 2068689Notes

Reaction equation

HRID 2068689 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH:7]([CH3:11])[C:8]([OH:10])=[O:9])[CH:6]=1.OS(O)(=O)=O.[CH3:17]O>>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH:7]([CH3:11])[C:8]([O:10][CH3:17])=[O:9])[CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 166406402-(4-Bromo-1H-pyrazol-1-yl)propanoic acid

Product 1

HCID 17024860methyl 2-(4-bromo-1H-pyrazol-1-yl)propanoateYield 82%

Conditions

Temperature
68 °C

Procedure

To a solution of 2-(4-bromo-1H-pyrazol-1-yl)propanoic acid (0.20 g, 0.91 mmol) in MeOH (4.0 mL) was added conc H2SO4 (0.20 mL) and the resulting reaction mixture was heated to 68° C. for 2 h. After the completion of reaction (TLC monitoring), the solvent was evaporated and the residue was basified with saturated NaHCO3 solution followed by extraction with EtOAc (3×25.0 mL). The combined organics was dried (Na2SO4), filtered and concentrated to obtain the desired product (0.175 g, 82%).

Workup

  1. customthe resulting reaction mixture
  2. customAfter the completion of reaction (TLC monitoring)
  3. customthe solvent was evaporated
  4. extractionfollowed by extraction with EtOAc (3×25.0 mL)
  5. dry with materialThe combined organics was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-02b4de01e03b4b78afdd206e51033658
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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