Reaktion #9329

Reaktionsgleichung

cyclobutanone

n-Butyllithium

1,4-dibromobenzene

→

3-1

Ausbeute 54.0%

1-(4-Bromo-phenyl)-cyclobutanol

Ausbeute 54.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenrinsing with 0.5 mL THF
2. 2
   workup.ADDITIONsaturated NH4Cl solution was added
3. 3
   ExtraktionThe resulting mixture was extracted with ethyl acetate (3×30 mL)
4. 4
   Waschenthe combined ethyl acetate solution was washed with brine
5. 5
   TrocknenThe solution was then dried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   SonstigePurification by flash chromatography on silica gel (5%→10% ethyl acetate/hexanes)

Vorschrift

n-Butyllithium (1.2 mL 1.92 mmol, 1.6 M/hexanes) was added to a −78° C. solution of 1,4-dibromobenzene (489 mg, 2.07 mmol) in THF (4.2 mL). After 30 min., a solution of cyclobutanone (141 mg, 2.01 mmol) in 1 mL THF was added by cannula, rinsing with 0.5 mL THF. The reaction was allowed to warm to room temperature and after 2 h, saturated NH4Cl solution was added. The resulting mixture was extracted with ethyl acetate (3×30 mL) and the combined ethyl acetate solution was washed with brine. The solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (5%→10% ethyl acetate/hexanes) gave 3-1 (235 mg, 54%).

Quelle