Réaction #1340567

Équation de réaction

dibenzo[f,h]quinoxaline

hexane

n-butyllithium

3-bromofluorobenzene

→

2-(3-Fluorophenyl)-dibenzo[f,h]quinoxaline

Rendement 23.0%

Solvants

dichloromethane

Water

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was heated to room temperature
2. 2
   workup.STIRRINGstirred for 12 hours with the temperature
3. 3
   Températuremaintained at room temperature
4. 4
   Extractionwas extracted
5. 5
   SéchageThe obtained organic layer was dried with anhydrous magnesium sulfate
6. 6
   AutreThe solution obtained by the drying
7. 7
   Filtrationwas filtrated
8. 8
   workup.DISTILLATIONThe solvent of this solution was distilled off
9. 9
   Autreby recrystallization with ethanol
10. 10
    Autrewas obtained (a light-orange powder, yield: 23%)
11. 11
    AutreSynthesis scheme of Step 1

Mode opératoire

First, under a nitrogen atmosphere, 27.5 mL (1.58 mol/L) of a hexane solution of n-butyllithium was dripped into a mixed solution of 6.87 g of 3-bromofluorobenzene and 40 mL of tetrahydrofuran at −78° C. Then, with the temperature maintained at −78° C., the mixture was stirred for 2 hours. To the obtained solution was added 7.54 g of dibenzo[f,h]quinoxaline in five additions at −78° C. The mixture was heated to room temperature,and stirred for 12 hours with the temperature maintained at room temperature. Water was added to this mixture and dichloromethane was used as an extraction solvent, so that an organic layer was extracted. The obtained organic layer was dried with anhydrous magnesium sulfate. The solution obtained by the drying was filtrated. The solvent of this solution was distilled off, and then, by recrystallization with ethanol, the organometallic complex of the present invention, Hdbq-3FP, which was the target substance, was obtained (a light-orange powder, yield: 23%). Synthesis scheme of Step 1 is shown in (a-2) below.

Source