Benzyl Bromide → 1-benzyl-1H-pyrazole-3-carbaldehyde

HRID 413283Notes

Reaction equation

HRID 413283 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:9]1[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[N:10]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([N:9]1[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[N:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 122183831H-Pyrazole-3-carbaldehyde

Product 1

HCID 114011991-benzyl-1H-pyrazole-3-carbaldehydeYield 61.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzyl bromide (0.29 g) in N,N-dimethylformamide (9 ml) was added 1H-pyrazole-3-carboxaldehyde (0.15 g) and potassium carbonate (0.24 g). The mixture was stirred at room temperature for 24 hours, silica gel was added, the solvent removed by evaporation and the crude material purified by chromatography (isohexane:ether, 2:1) to give the product as an oil (0.18 g).

Workup

  1. additionsilica gel was added
  2. customthe solvent removed by evaporation
  3. customthe crude material purified by chromatography (isohexane:ether, 2:1)

Sources & evidence

ORD record
ord-6d33378c29d04b489b7fbd4671e4aa97
Source dataset
uspto-grants-2003_05
Patent number
US06566376B1

Reaction notes

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