Reaktion #2314308

Reaktionsgleichung

9H-tribenz[b,d,f]azepine

1,4-dibromobenzene

decalin

potassium hydroxide

→

9-(4-bromophenyl)-9H-tribenz[b,d,f]azepine

Ausbeute 25.1%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled nearly to room temperature
2. 2
   Filtrationfollowed by filtration
3. 3
   Sonstigeto remove the insoluble matter
4. 4
   EinengenThe filtrate was concentrated
5. 5
   SonstigeTo remove decalin, n-hexane
6. 6
   workup.ADDITIONwas added to the residue
7. 7
   Filtrationfollowed by filtration
8. 8
   SonstigeThe filter cake was purified by silica gel column chromatography

Vorschrift

A mixture of 9.2 g (38 mmol) of 9H-tribenz[b,d,f]azepine (synthesized in accordance with J. Org. Chem., vol. 56, p. 3906 (1991)), 44.8 g (190 mmol) of 1,4-dibromobenzene, 5.6 g (100 mmol) of potassium hydroxide, 1.6 g (25 mmol) of copper powder, and 50 ml of decalin was heated at an external temperature of 200° C. for 36 hours in a nitrogen stream while stirring. The reaction mixture was cooled nearly to room temperature, chloroform was added thereto, followed by filtration using Celite to remove the insoluble matter. The filtrate was concentrated. To remove decalin, n-hexane was added to the residue, followed by filtration. The filter cake was purified by silica gel column chromatography to give 3.8 g (25%) of 9-(4-bromophenyl)-9H-tribenz[b,d,f]azepine.

Quelle