Reaktion #1724833

Reaktionsgleichung

4-phenyl-benzylchloride

3-bromo-9H-carbazole

sodium hydride

→

9-(biphenyl-4-ylmethyl)-3-bromo-9H-carbazole

Ausbeute 100.0%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction mixture
2. 2
   workup.STIRRINGwas stirred at room temperature for 20 h
3. 3
   workup.ADDITIONpoured onto water (300 ml)
4. 4
   workup.STIRRINGstirred for 4 h
5. 5
   FiltrationThe precipitate was filtered off
6. 6
   Waschenwashed with water (3×150 ml)
7. 7
   Sonstigedried in vacuo at 50° C. for 18 h
8. 8
   WaschenThe crude product was washed with heptane
9. 9
   Filtrationfiltered off
10. 10
    Sonstigedried in vacuo at 50° C.

Vorschrift

To a solution of 3-bromo-9H-carbazole (7.38 g, 30 mmol, prepared as described in Tetrahedron (1992), 48, 4779) in N,N-dimethylformamide (200 ml) was added portion wise sodium hydride (1.6 g, 39 mmol, 60% in mineral oil) during 15 min. After stirring at room temperature for 1 h, 4-phenyl-benzylchloride (6.21 g, 30 mmol) was added portion wise during 10 min. The resulting reaction mixture was stirred at room temperature for 20 h poured onto water (300 ml) and stirred for 4 h. The precipitate was filtered off, washed with water (3×150 ml) and dried in vacuo at 50° C. for 18 h. The crude product was washed with heptane, filtered off and dried in vacuo at 50° C. affording 12 g (100%) of 9-(biphenyl-4-ylmethyl)-3-bromo-9H-carbazole as a solid.

Quelle