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

HRID 1360446Notes

Reaction equation

HRID 1360446 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-6ef1de77c65349d0bc5871f51cf723d1
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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