Reaktion #473545

Reaktionsgleichung

dibromochrysene aniline

P(t-Bu)3

dibromochrysene

4-iso-propylaniline

sodium tert-butoxide

→

N,N′-bis(4-iso-propylphenyl)-chrysene-6,12-diamine

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter ten minutes of stirring
2. 2
   Sonstigecapped with a nitrogen inlet
3. 3
   workup.STIRRINGstirred in an 80° C. oil bath overnight (18 h)
4. 4
   SonstigeNext day, reaction mixture
5. 5
   workup.ADDITIONpoured onto 15 g of silica gel and 15 g of celite
6. 6
   Sonstigeswirled around for a few minutes
7. 7
   Filtrationfiltered through a 4 inch plug of silica gel
8. 8
   Waschenwashing with 5.5 liters of toluene
9. 9
   SonstigeVolatiles were removed under vacuum
10. 10
    Sonstigeto give a dark yellow solid
11. 11
    SonstigeThe solid was triturated with diethyl ether, vacuum
12. 12
    Filtrationfiltered
13. 13
    Waschenwashed with minimal amount of ether
14. 14
    SonstigeThe resulting yellow solid was dried on a high vacuum line

Vorschrift

In the drybox, a 500 mL one-neck round-bottom flask was charged with dibromochrysene (9 g, 23.3 mmol), 4-iso-propylaniline (6.61 g, 48.9 mmol) and 200 mL of dry toluene. In a separate 100 ml flask, Pd2(dba)3 (0.192 g, 0.21 mmol), P(t-Bu)3 (0.085 g, 0.42 mmol) were dissolved in 25 ml of dry toluene, stirred for 10 minutes and then added to the dibromochrysene/aniline solution. After ten minutes of stirring, sodium tert-butoxide (4.48 g, 46.6 mmol) was added in one portion. The reaction flask was brought out of the drybox, capped with a nitrogen inlet and stirred in an 80° C. oil bath overnight (18 h). Next day, reaction mixture was cooled to room temperature, poured onto 15 g of silica gel and 15 g of celite, swirled around for a few minutes and filtered through a 4 inch plug of silica gel, washing with 5.5 liters of toluene. Volatiles were removed under vacuum to give a dark yellow solid. The solid was triturated with diethyl ether, vacuum filtered and washed with minimal amount of ether. The resulting yellow solid was dried on a high vacuum line. Yield 8.68 g (75.5%). The compound was confirmed by NMR analysis.

Quelle