Methyl iodide → 4-Bromo-1,3,5-trimethylpyrazole

HRID 2802

Reaction equation

HRID 2802 reaction equation
[Br:1][C:2]1[C:3]([CH3:8])=[N:4][NH:5][C:6]=1[CH3:7].[H-].[Na+].[H][H].IC.[C:15](=O)([O-])O.[Na+]>CN(C)C=O>[Br:1][C:2]1[C:3]([CH3:8])=[N:4][N:5]([CH3:15])[C:6]=1[CH3:7]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 769374-bromo-3,5-dimethyl-1H-pyrazoleHCID 516892Sodium BicarbonateHCID 178418361HCID 178418361, compound

Product 1

HCID 5191814-Bromo-1,3,5-trimethylpyrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Bromo-3,5-dimethylpyrazole (10 g) in dry dimethylformamide (50 ml) was added to a stirred suspension of sodium hydride (1.8 g) in dry dimethylformamide at 0° C. When the evolution of hydrogen was complete, iodomethane (8.9 g) was added dropwise. The mixture was allowed to warm to room temperature and after 30 minutes saturated aqueous sodium hydrogen carbonate (5 ml) was added. Following evaporation under high vacuum, the residue was purified by column chromatography to give the title compound.

Workup

  1. additionwas added
  2. customevaporation under high vacuum
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ac7f5eb35ef547d1a557dea38319f19e
Source dataset
uspto-grants-1998_03
Patent number
US05731335

Linked notes

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