Reaction #2487421

Reaction equation

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

Solvents

water

toluene

dioxane

Conditions

Workup

1. 1
   Otherdegassed
2. 2
   Temperaturethe mixture is refluxed for 60 h
3. 3
   TemperatureAfter cooling
4. 4
   Otherthe organic phase is separated off
5. 5
   Washwashed three times with 200 ml of water
6. 6
   Dryingonce 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
   Otherthe organic phase is evaporated to dryness under reduced pressure in a rotary evaporator
9. 9
   OtherThe grey residue obtained in this way
10. 10
    Otheris recrystallised from dioxane
11. 11
    FiltrationThe deposited crystals are filtered off with suction
12. 12
    Washwashed with 50 ml of ethanol
13. 13
    Othersubsequently dried under reduced pressure

Procedure

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