Bromine → 4-bromo-5-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile

HRID 1360429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360429
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:10]([CH2:11][CH3:12])[N:9]=[C:8]([C:13]#[N:14])[CH:7]=1.C([O-])(=O)C.[K+].[Br:20]Br>C(O)(=O)C>[Br:20][C:7]1[C:8]([C:13]#[N:14])=[N:9][N:10]([CH2:11][CH3:12])[C:6]=1[CH2:5][CH2:4][CH2:3][CH2:2][Cl:1]

Komponenten

5

Edukt 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 669589675-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile

Produkt 1

HCID 669582654-bromo-5-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

5-(4-Chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile (10.8 g, 51.0 mmol) was treated with potassium acetate (10.0 g, 102 mmol) and bromine (2.9 mL, 56 mmol) in acetic acid (102 mL), and the reaction was stirred overnight at ambient temperature. The acetic acid was removed under reduced pressure, and the residue was partitioned between water and chloroform. The mixture was adjusted to pH 10 with the addition of 2 N aqueous sodium carbonate. The aqueous layer was extracted with chloroform, and the combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting yellow oil was purified by chromatography on a HORIZON HPFC system (eluting with hexanes/ethyl acetate in a gradient from 95:5 to 50:50) to provide 4-bromo-5-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile.

Aufarbeitung

  1. customThe acetic acid was removed under reduced pressure
  2. customthe residue was partitioned between water and chloroform
  3. additionThe mixture was adjusted to pH 10 with the addition of 2 N aqueous sodium carbonate
  4. extractionThe aqueous layer was extracted with chloroform
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting yellow oil was purified by chromatography on a HORIZON HPFC system (
  9. washeluting with hexanes/ethyl acetate in a gradient from 95:5 to 50:50)

Quellen und Nachweise

ORD-Eintrag
ord-f47ea33fc2944382860d8df65b8bb315
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879849B2

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