4-Bromoaniline → 1-(4-Bromophenyl)-2-(3-fluoro-4-(methylsulfonyl)phenyl]-5-methyl-1H-pyrrole

HRID 396746Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 396746
[F:1][C:2]1[CH:3]=[C:4]([C:12](=O)[CH2:13][CH2:14][C:15](=O)[CH3:16])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[Br:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:19][C:20]1[CH:26]=[CH:25][C:23]([N:24]2[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]2[C:4]2[CH:5]=[CH:6][C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[C:2]([F:1])[CH:3]=2)=[CH:22][CH:21]=1

Komponenten

5

Edukt 2

HCID 78074-BromoanilineHCID 223169711-[3-Fluoro-4-(methylsulfonyl)phenyl]pentane-1,4-dione

Produkt 1

HCID 223168021-(4-Bromophenyl)-2-(3-fluoro-4-(methylsulfonyl)phenyl]-5-methyl-1H-pyrroleAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 1-[3-fluoro-4-(methylsulfonyl)phenyl]pentane-1,4-dione (2.8 g, 10.3 mmol), 4-bromoaniline (2.12 g, 12.3 mmol), and p-toluenesulfonic acid (150 mg) in toluene (250 mL) was heated at reflux temperature using Dean-Stark apparatus. After cooling down, volatiles were removed by evaporation. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/5) to give the subtitle compound (4 g, 95% yield).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux temperature
  3. temperatureAfter cooling down
  4. customvolatiles were removed by evaporation
  5. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/5)

Quellen und Nachweise

ORD-Eintrag
ord-4dbc78fcc03e49e7ae103de681de1ab9
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608095B2

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