Réaction #2487421

Équation de réaction

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

Solvants

water

toluene

dioxane

Conditions de réaction

Traitement

1. 1
   Autredegassed
2. 2
   Températurethe mixture is refluxed for 60 h
3. 3
   TempératureAfter cooling
4. 4
   Autrethe organic phase is separated off
5. 5
   Lavagewashed three times with 200 ml of water
6. 6
   Séchageonce 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
   Autrethe organic phase is evaporated to dryness under reduced pressure in a rotary evaporator
9. 9
   AutreThe grey residue obtained in this way
10. 10
    Autreis recrystallised from dioxane
11. 11
    FiltrationThe deposited crystals are filtered off with suction
12. 12
    Lavagewashed with 50 ml of ethanol
13. 13
    Autresubsequently dried under reduced pressure

Mode opératoire

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.

Source