Reacción #1885006

Ecuación de reacción

1-naphthylboronic acid

2,5-dibromonitrobenzene

potassium carbonate

→

1-nitro-2,5-dinaphth-1-ylbenzene

Disolventes

water

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrodegassed
2. 2
   Temperaturathe mixture is heated
3. 3
   Temperaturaunder reflux for 20 h
4. 4
   TemperaturaAfter cooling
5. 5
   Otrothe organic phase is separated off
6. 6
   Lavadowashed three times with 200 ml of water
7. 7
   Secadoonce with 200 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
    Otrosubsequently dried in vacuo

Procedimiento

2.4 g (2.1 mmol) of Pd(PPh3)4 are added to a well-stirred, degassed suspension of 67.8 g (190 mmol) of 1-naphthylboronic acid, 53.3 g (190 mmol) of 2,5-dibromonitrobenzene and 137.9 g (648.5 mmol) of potassium carbonate in a mixture of 250 ml of water and 250 ml of THF, and the mixture is heated under reflux for 20 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, 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 subsequently dried in vacuo; yield: 86.1 g, 71% of theory; purity: 98.4% according to HPLC.

Fuente