1,4-Dibromobutane → 4-(4-Bromobutyl)-1-(1,3-dithian-2-yl)ethylbenzene

HRID 266993

Reaktionsgleichung

Reaktionsgleichung von HRID 266993
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:10]2[S:15][CH2:14][CH2:13][CH2:12][S:11]2)[CH3:9])=[CH:4][CH:3]=1.C([Li])(CC)C.[Br:21][CH2:22][CH2:23][CH2:24][CH2:25]Br.C(OCC)(=O)C>O1CCCC1>[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:10]2[S:15][CH2:14][CH2:13][CH2:12][S:11]2)[CH3:9])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 80561,4-DibromobutaneHCID 8857Ethyl AcetateHCID 219601124-Bromo-1-(1,3-dithian-2-yl)ethylbenzeneHCID 178418400CID 53628100

Produkt 1

HCID 219601294-(4-Bromobutyl)-1-(1,3-dithian-2-yl)ethylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-bromo-1-(1,3-dithian-2-yl)ethylbenzene (27.2 g, 94 mmol) in tetrahydrofuran (200 ml) was charged with sec-butyllithium (99 ml, 1.3M in cyclohexane, 0.13 mole) dropwise at -78° C. under nitrogen. The mixture was stirred at ambient temperature for 1.5 hours, and then quenched with 1,4-dibromobutane (42 g, 0.2 mole). After being stirred for 3 hours, the mixture was poured into ethyl acetate, and then washed with water and brine. The organic solution was then dried (Na2SO4) and concentrated to an oil. The crude product was purified by flash chromatography over a silica gel column. The 4-(4-bromobutyl)-1-(1,3-dithian-2-yl)-ethylbenzene thus purified was a light oil, 22.3 g.

Aufarbeitung

  1. stirringAfter being stirred for 3 hours
  2. washwashed with water and brine
  3. dry with materialThe organic solution was then dried (Na2SO4)
  4. concentrationconcentrated to an oil
  5. customThe crude product was purified by flash chromatography over a silica gel column
  6. customThe 4-(4-bromobutyl)-1-(1,3-dithian-2-yl)-ethylbenzene thus purified

Quellen und Nachweise

ORD-Eintrag
ord-ed8fba15c4a645598a0f337106839cd0
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05652241

Verknüpfte Notizen

Wird geladen…