4-Methylpyrazole → 2-(4-Methylpyrazol-1-yl)benzaldehyde

HRID 1966706Notes

Reaction equation

HRID 1966706 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:10][C:11]1[CH:12]=[N:13][NH:14][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:10][C:11]1[CH:12]=[N:13][N:14]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[CH:15]=1

Participants

5

Reactant 3

HCID 34064-MethylpyrazoleHCID 11430Potassium CarbonateHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 585420752-(4-Methylpyrazol-1-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

2-Fluorobenzaldehyde (250 mg, 2.01 mmol), 4-methyl-1H-pyrazole (260 mg, 3.17 mmol) and potassium carbonate (820 mg, 5.93 mmol) are combined in DMSO (15 mL) and warmed to 100° C. for 18 hours. The reaction mixture is cooled to room temperature and the potassium carbonate is removed via filtration. The solids are washed with EtOAc and the combined filtrates are poured into water. Separate the layers and extract the aqueous phase with EtOAc (1×). The combined organics are washed with water and brine and dried (MgSO4), filtered, and concentrated. Purification via flash chromatography (12 g silica gel, 0-15% EtOAc/heptane) gives 2-(4-methyl-pyrazol-1-yl)-benzaldehyde.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customthe potassium carbonate is removed via filtration
  3. washThe solids are washed with EtOAc
  4. additionthe combined filtrates are poured into water
  5. customSeparate the layers
  6. extractionextract the aqueous phase with EtOAc (1×)
  7. washThe combined organics are washed with water and brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification via flash chromatography (12 g silica gel, 0-15% EtOAc/heptane)

Sources & evidence

ORD record
ord-d3cc54e042474f5ca689832a03920bcd
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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