Bromine → 4-bromo-1,5-dimethyl-1H-pyrazole-3-carbonitrile

HRID 1984325Notes

Reaction equation

HRID 1984325 reaction equation
[Br:1]Br.C([O-])(=O)C.[K+].[CH3:8][N:9]1[C:13]([CH3:14])=[CH:12][C:11]([C:15]#[N:16])=[N:10]1.S([O-])(O)=O.[Na+]>C(O)(=O)C>[Br:1][C:12]1[C:11]([C:15]#[N:16])=[N:10][N:9]([CH3:8])[C:13]=1[CH3:14]

Participants

6

Reactant 4

HCID 24408BromineHCID 517044Potassium AcetateHCID 122118911,5-dimethyl-1H-pyrazole-3-carbonitrileHCID 23665763Sodium Bisulfite

Product 1

HCID 669589664-bromo-1,5-dimethyl-1H-pyrazole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (5.1 g, 32 mmol) in acetic acid (10 mL) was added dropwise to a solution of potassium acetate (3.9 g, 40 mmol) and 1,5-dimethyl-1H-pyrazole-3-carbonitrile in acetic acid (50 mL). Following the addition, the reaction was stirred for 30 minutes. Saturated aqueous sodium hydrogensulfite was added, and the mixture was stirred until it became colorless. The volatiles were removed under reduced pressure, and the residue was stirred with water to form a solid. The solid was isolated by filtration, washed with water, and recrystallized from ethanol and then from hexane to provide 2.5 g of 4-bromo-1,5-dimethyl-1H-pyrazole-3-carbonitrile as colorless needles, mp 92-94° C.

Workup

  1. additionthe addition
  2. stirringthe mixture was stirred until it
  3. customThe volatiles were removed under reduced pressure
  4. stirringthe residue was stirred with water
  5. customto form a solid
  6. customThe solid was isolated by filtration
  7. washwashed with water
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a9dfe3af2d7842e6aafa4a95ce28418f
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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