Acetone → 2-(3,5-Dibromothiophen-2-yl)propan-2-ol

HRID 23464

Reaktionsgleichung

Reaktionsgleichung von HRID 23464
Br[C:2]1[S:3][C:4]([Br:8])=[CH:5][C:6]=1[Br:7].CCCCCC.[Li]CCCC.[CH3:20][C:21]([CH3:23])=[O:22]>CCOCC>[Br:7][C:6]1[CH:5]=[C:4]([Br:8])[S:3][C:2]=1[C:21]([OH:22])([CH3:23])[CH3:20]

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 8058HexaneHCID 76592Thiophene, 2,3,5-tribromo-HCID 178418339Butyllithium

Produkt 1

HCID 225727272-(3,5-Dibromothiophen-2-yl)propan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 2,3,5-tribromothiophene (8.17 g, 25 mmol) in Et2O (N2 atmosphere) was cooled to −78° C. and treated with a 1.6 M hexane solution of nBuLi (15.6 mL, 25 mmol). The mixture was then stirred for 10 minutes, then treated with acetone (1.84 mL, 25 mmol). The mixture was then stirred for 30 minutes and quenched with H2O. The mixture was extracted with Et2O; the organic layers were combined, dried (MgSO4), and the solvent removed in vacuo. The residue was filtered through a plug of silica gel (gradient elution from hexanes to EtOAc) to provide the title compound.

Aufarbeitung

  1. stirringThe mixture was then stirred for 30 minutes
  2. customquenched with H2O
  3. extractionThe mixture was extracted with Et2O
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. filtrationThe residue was filtered through a plug of silica gel (gradient elution from hexanes to EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-eddf34b407b548debb99d9803b0c57a1
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852711B2

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