Reaktion #1277414

Reaktionsgleichung

tri-o-tolylphosphine

4-methylnaphthalene-1-boronic acid

9-bromoanthracene

tripotassium phosphate

→

9-(4-Methylnaphth-1-yl)anthracene

Lösungsmittel

dioxane

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture is refluxed for 16 h
2. 2
   TemperaturAfter the reaction mixture has been cooled
3. 3
   Sonstigethe organic phase is separated off
4. 4
   Waschenwashed three times with 500 ml of water
5. 5
   FiltrationThe organic phase is subsequently filtered through silica gel
6. 6
   Sonstigeevaporated to dryness
7. 7
   workup.DISSOLUTIONdissolved
8. 8
   Temperaturunder reflux
9. 9
   TemperaturAfter cooling
10. 10
    Filtrationthe colourless solid is filtered off with suction
11. 11
    Waschenagain washed
12. 12
    Sonstigefinally dried under reduced pressure

Vorschrift

3.6 g (11.7 mmol) of tri-o-tolylphosphine and then 437 mg (1.9 mmol) of palladium(II) acetate are added with vigorous stirring to a suspension of 93.0 g (500 mmol) of 4-methylnaphthalene-1-boronic acid, 100.0 g (389 mmol) of 9-bromoanthracene, 212.3 g (1 mol) of tripotassium phosphate in a mixture of 400 ml of dioxane, 600 ml of toluene and 1000 ml of water, and the mixture is refluxed for 16 h. After the reaction mixture has been cooled, the organic phase is separated off and washed three times with 500 ml of water. The organic phase is subsequently filtered through silica gel and evaporated to dryness. The oil which remains is taken up in 1000 ml of ethanol and dissolved under reflux. After cooling, the colourless solid is filtered off with suction, again washed by stirring with 1000 ml of ethanol and finally dried under reduced pressure. Yield: 103.0 g (83.1% of theory), about 96% according to 1H-NMR.

Quelle