Reaktion #2487421

Reaktionsgleichung

tri-o-tolylphosphine

4-trimethylsilyinaphth-1-ylboronic acid

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

tripotassium phosphate

→

9-(4-methylnaphth-1-yl)-10-(4-trimethylsilyinaphthyl)anthracene

Lösungsmittel

water

toluene

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedegassed
2. 2
   Temperaturthe mixture is refluxed for 60 h
3. 3
   TemperaturAfter cooling
4. 4
   Sonstigethe organic phase is separated off
5. 5
   Waschenwashed three times with 200 ml of water
6. 6
   Trocknenonce with 200 ml of saturated aqueous sodium chloride solution and subsequently dried over magnesium sulfate
7. 7
   FiltrationAfter the desiccant has been filtered off
8. 8
   Sonstigethe organic phase is evaporated to dryness under reduced pressure in a rotary evaporator
9. 9
   SonstigeThe grey residue obtained in this way
10. 10
    Sonstigeis recrystallised from dioxane
11. 11
    FiltrationThe deposited crystals are filtered off with suction
12. 12
    Waschenwashed with 50 ml of ethanol
13. 13
    Sonstigesubsequently dried under reduced pressure

Vorschrift

1.78 g (5.6 mmol) of tri-o-tolylphosphine and 0.2 g (0.9 mmol) of palladium acetate are added to a vigorously stirred, degassed suspension of 22.8 g (93.3 mmol) of 4-trimethylsilyinaphth-1-ylboronic acid, 37.4 g (93.3 mmol) of 9-(4-methylnaphth-1-yl)anthracene and 90 g (230 mmol) of tripotassium phosphate in a mixture of 575 ml of water, 100 ml of dioxane and 860 ml of toluene, and the mixture is refluxed for 60 h. After cooling, the organic phase is separated off, washed three times with 200 ml of water and once with 200 ml of saturated aqueous sodium chloride solution and subsequently dried over magnesium sulfate. After the desiccant has been filtered off, the organic phase is evaporated to dryness under reduced pressure in a rotary evaporator. The grey residue obtained in this way is recrystallised from dioxane. The deposited crystals are filtered off with suction, washed with 50 ml of ethanol and subsequently dried under reduced pressure; yield: 38 g, 79% of theory; purity: 99.9% according to HPLC.

Quelle