Reacción #1885005

Ecuación de reacción

1-naphthylboronic acid

4-bromo-2-nitrobiphenyl

potassium carbonate

→

4-naphth-1-yl-2-nitrobiphenyl

Disolventes

water

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrodegassed
2. 2
   Temperaturathe mixture is heated
3. 3
   Temperaturaunder reflux for 17 h
4. 4
   TemperaturaAfter cooling
5. 5
   Otrothe organic phase is separated off
6. 6
   Lavadowashed three times with 400 ml of water
7. 7
   Secadoonce with 400 ml of saturated, aqueous sodium chloride solution, dried over magnesium sulfate
8. 8
   Otroevaporated to dryness in vacuo in a rotary evaporator
9. 9
   OtroThe grey residue is recrystallised from hexane
10. 10
    FiltraciónThe deposited crystals are filtered off with suction
11. 11
    Lavadowashed with a little MeOH
12. 12
    Otrodried in vacuo

Procedimiento

1.62 g (1.40 mmol) of Pd(PPh3)4 are added to a well-stirred, degassed suspension of 46 g (268 mmol) of 1-naphthylboronic acid, 71 g (255.3 mmol) of 4-bromo-2-nitrobiphenyl and 93 g (433.9 mmol) of potassium carbonate in a mixture of 700 ml of water and 700 ml of THF, and the mixture is heated under reflux for 17 h. After cooling, the organic phase is separated off, washed three times with 400 ml of water and once with 400 ml of saturated, aqueous sodium chloride solution, dried over magnesium sulfate and evaporated to dryness in vacuo in a rotary evaporator. The grey residue is recrystallised from hexane. The deposited crystals are filtered off with suction, washed with a little MeOH and dried in vacuo; yield: 83.1 g, 97.9% of theory; purity: 99.0% according to HPLC.

Fuente