Sodium Carbonate → 1-Benzyl-4-bromo-5-methyl-1H-pyrazole-3-carbonitrile

HRID 1984370Notes

Reaction equation

HRID 1984370 reaction equation
[CH2:1]([N:8]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]#[N:15])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].[Br:21]Br.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([Br:21])[C:10]([C:14]#[N:15])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24408BromineHCID 517044Potassium AcetateHCID 66958933HCID 66958933, compound

Product 1

HCID 669586391-Benzyl-4-bromo-5-methyl-1H-pyrazole-3-carbonitrileYield 95.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-Benzyl-5-methyl-1H-pyrazole-3-carbonitrile (3.38 g, 17.1 mmol) was treated with potassium acetate (2.35 g, 24.0 mmol) and bromine (3.01 g, 18.9 mmol) in glacial acetic acid (48 mL) according to the method described in Part F of Examples 1-4. After the 2 M aqueous sodium carbonate was added in the work-up, a white solid was isolated by filtration and washed with water to yield 4.49 g of 1-benzyl-4-bromo-5-methyl-1H-pyrazole-3-carbonitrile.

Workup

  1. customa white solid was isolated by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-af686c273c644abf99b0bed9148edd0a
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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