p-Toluenesulfonic acid → 1-(3-bromophenyl)-2,5-dimethyl-1H-pyrrole

HRID 1994117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1994117
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C[C:10]1[CH:11]=[CH:12][C:13](S(O)(=O)=O)=[CH:14][CH:15]=1>C(CC(=O)C)C(C)=O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([N:5]2[C:14]([CH3:13])=[CH:15][CH:10]=[C:11]2[CH3:12])[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 115623-Bromoaniline

Produkt 1

HCID 47636541-(3-bromophenyl)-2,5-dimethyl-1H-pyrroleAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 80352,5-HexanedioneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 3-bromoaniline (2.50 mL, 23.0 mmol) in acetonylacetone (3.00 mL, 25.6, mmol) containing a small amount of p-TSA was heated at reflux in a round bottom flask fitted with a Dean Stark trap and a reflux condenser for 5 h. The reaction mixture was allowed to cool to rt and diluted with EtOAc. The solution was washed with 1N HCl and sat. NaHCO3 solution. The organic solutions were dried over Na2SO4, filtered, and concentrated to give the desired product as a light brown solid (5.5 g, 96%) which was used without further purification.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux in a round bottom flask
  3. customfitted with a Dean Stark trap and a reflux condenser for 5 h
  4. washThe solution was washed with 1N HCl and sat. NaHCO3 solution
  5. dry with materialThe organic solutions were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-85da1545317a4534bbc5d18252565280
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652041B2

Notizen zur Reaktion

Wird geladen…