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

HRID 2283771Notes

Reaction equation

HRID 2283771 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-734ad4b2def940fd82bdb8bef75dcd93
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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