p-Toluenesulfonic acid → 1-(4-Bromophenyl)-2,3-dimethyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole

HRID 2086636

Reaktionsgleichung

Reaktionsgleichung von HRID 2086636
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][CH:13]([CH3:17])[C:14](=O)[CH3:15])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Br:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:19][C:20]1[CH:26]=[CH:25][C:23]([N:24]2[C:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)=[CH:12][C:13]([CH3:17])=[C:14]2[CH3:15])=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 78074-BromoanilineHCID 218628391-[4-(Methylsulfonyl)phenyl]-3-methylpentane-1,4-dione

Produkt 1

HCID 223167681-(4-Bromophenyl)-2,3-dimethyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrroleAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 1-[4-(methylsulfonyl)phenyl]-3-methylpentane-1,4-dione (110 mg, 0.41 mmol), 4-bromoaniline (71 mg, 0.41 mmol), and p-toluenesulfonic acid (10 mg) in toluene (3 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 (1/3) to give the subtitle compound (110 mg, 67% 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 (1/3)

Quellen und Nachweise

ORD-Eintrag
ord-c7278dd3ad674d788e35fe92c9e9d5ac
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06727238B2

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