Reaktion #83907

Reaktionsgleichung

ethyl acetate

1,4-dibromobutane

4-bromo-1-(1,3-dithian-2-yl)ethylbenzene

sec-butyllithium

→

4-(4-bromobutyl)-1-(1,3-dithian-2-yl)ethylbenzene

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter being stirred for 3 hours
2. 2
   Waschenwashed with water and brine
3. 3
   TrocknenThe organic solution was then dried (Na2SO4)
4. 4
   Einengenconcentrated to an oil
5. 5
   SonstigeThe crude product was purified by flash chromatography over a silica gel column
6. 6
   SonstigeThe 4-(4-bromobutyl)-1-(1,3-dithian-2-yl)-ethylbenzene thus purified

Vorschrift

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.

Quelle