Reaktion #1511951

Reaktionsgleichung

Butyllithium

N-(2-bromophenyl)-N-(3-bromophenyl)-3′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-3-amine

Dichlorodiphenylsilane

dry ice

→

Compound 10

5-(3′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-3-yl)-10,10-diphenyl-5,10-dihydrodibenzo[b,e][1,4]azasiline

Lösungsmittel

Acetone

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto slowly warm to room temperature
2. 2
   workup.STIRRINGwas stirred overnight
3. 3
   SonstigeThe reaction was quenched with water
4. 4
   Extraktionextracted three times with ether
5. 5
   Waschenwashed with brine and water
6. 6
   SonstigeThe crude material was purified with column chromatography
7. 7
   SonstigeThe product was collected as a white powder with a purity of 99.3% by HPLC
8. 8
   SonstigeThe product was recrystallized twice from DCM and hexane

Vorschrift

N-(2-bromophenyl)-N-(3-bromophenyl)-3′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-3-amine was added into a 250 mL round bottom flask, and solubilized in dry THF (155 ml). The solution was cooled down to −78° C. using dry ice and Acetone. Butyllithium (7.45 ml, 18.62 mmol) was added dropwise and the reaction mixture was stirred −78° C. for 2 hours. Dichlorodiphenylsilane (2.108 ml, 10.24 mmol) was then added dropwise. The reaction mixture was allowed to slowly warm to room temperature and was stirred overnight. The reaction was quenched with water, extracted three times with ether, washed with brine and water. The crude material was purified with column chromatography using hexane/DCM (75/25). The product was collected as a white powder with a purity of 99.3% by HPLC. The product was recrystallized twice from DCM and hexane. The target 5-(3′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-3-yl)-10,10-diphenyl-5,10-dihydrodibenzo[b,e][1,4]azasiline (Compound 10) was afforded as a white powder (1.8 g, 29% yield). Compound 10 was then sublimed and 1.2 g was collected.

Quelle