2-Bromo-6-fluorobenzaldehyde → 1-(3-bromo-2-formylphenyl)-1H-pyrazole-3-carbonitrile

HRID 1025609Notes

Reaction equation

HRID 1025609 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]#[N:7])=[N:2]1.CC(C)([O-])C.[K+].[Br:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19](F)[C:16]=1[CH:17]=[O:18]>CS(C)=O>[Br:14][C:15]1[C:16]([CH:17]=[O:18])=[C:19]([N:1]2[CH:5]=[CH:4][C:3]([C:6]#[N:7])=[N:2]2)[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 224739772-Bromo-6-fluorobenzaldehydeHCID 23665647Potassium tert-butoxideHCID 178510229HCID 178510229, compound

Product 1

HCID 866737201-(3-bromo-2-formylphenyl)-1H-pyrazole-3-carbonitrileYield 73%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1H-pyrazole-3-carbonitrile (850 mg, 9.13 mmol) was dissolved in 15 mL of dry DMSO and potassium tert-butoxide (1.08 g, 9.13 mmol, Eq: 1.00) was added. The mixture was stirred at room temperature for 20 minutes and 2-bromo-6-fluorobenzaldehyde (3.71 g, 18.3 mmol, Eq: 2) was added. The mixture was stirred at room temperature overnight and then extracted with ethyl acetate and water. The organic layer was dried and concentrated. The crude material was purified by flash chromatography (silica gel, 40 g, 20% to 40% EtOAc in hexanes) to give 1-(3-bromo-2-formylphenyl)-1H-pyrazole-3-carbonitrile (1.83 g, 73%).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate and water
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customThe crude material was purified by flash chromatography (silica gel, 40 g, 20% to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9c0e6d278a6e4fe381867c40f1e8b510
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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