1,4-Dibromo-2-fluorobenzene → 1-(2,5-dibromophenyl)-3-methyl-1H-pyrazole

HRID 1499100

Reaktionsgleichung

Reaktionsgleichung von HRID 1499100
CC(C)([O-])C.[K+].[CH3:7][C:8]1[CH:12]=[CH:11][NH:10][N:9]=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:15]=1F>CS(C)=O>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:15]=1[N:10]1[CH:11]=[CH:12][C:8]([CH3:7])=[N:9]1

Komponenten

5

Edukt 3

HCID 1370041,4-Dibromo-2-fluorobenzeneHCID 23665647Potassium tert-butoxideHCID 178428694HCID 178428694, Verbindung

Produkt 1

HCID 1179420861-(2,5-dibromophenyl)-3-methyl-1H-pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Potassium t-butoxide (16.3 g, 145 mmol) was dissolved in DMSO (100 mL). To this solution was added 3-methylpyrazole (10.4 g, 120 mmol) and the reaction was heated at 50° C. for 30 min. 1,4-Dibromo-2-fluorobenzene (31 g, 120 mmol) was then added and the reaction stirred at 50° C. for 16 h. The reaction was cooled to RT and extracted with water and EtOAc, washed with brine, dried over Na2SO4, and then filtered and concentrated in vacuo. Purification by normal phase silica gel column chromatography (EtOAc/heptane) provided 1-(2,5-dibromophenyl)-3-methyl-1H-pyrazole.

Aufarbeitung

  1. temperatureThe reaction was cooled to RT
  2. extractionextracted with water and EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by normal phase silica gel column chromatography (EtOAc/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-901aa5158b204eef8b30ba18c6c6783d
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199994B2

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