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

HRID 1984325

Reaktionsgleichung

Reaktionsgleichung von HRID 1984325
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a9dfe3af2d7842e6aafa4a95ce28418f
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544697B2

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