Lawesson's reagent → 2-(3-Bromo-phenyl)-5-methyl-thiophene

HRID 551123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 551123
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][CH2:10][C:11](=O)[CH3:12])[CH:5]=[CH:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[S:24][C:11]([CH3:12])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 393572221-(3-Bromo-phenyl)-pentane-1,4-dione

Produkt 1

HCID 598296762-(3-Bromo-phenyl)-5-methyl-thiopheneAusbeute 66,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirring solution of 1-(3-bromo-phenyl)-pentane-1,4-dione (18.32 mmol) in toluene (90 mL) was added Lawesson's Reagent (19.24 mmol, 1.05 eq.) and the mixture was heated to reflux for 20 min. The reaction mixture was then cooled to room temperature and diluted with 1:1 hexanes/ether (90 mL) resulting in a precipitate. The mixture was filtered through a small pad of celite and the filtrate was concentrated to a light yellow solid that was purified by recrystallization from hexanes to give the final product as a white solid (12.17 mmol, 66%). MS (ESI) m/z 254.3.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 20 min
  3. customresulting in a precipitate
  4. filtrationThe mixture was filtered through a small pad of celite
  5. concentrationthe filtrate was concentrated to a light yellow solid
  6. customthat was purified by recrystallization from hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d53184b5b0444919af315872bf7cbf4a
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947712B2

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