Реакция #1885006

Уравнение реакции

1-naphthylboronic acid

2,5-dibromonitrobenzene

potassium carbonate

→

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

Растворители

water

THF

Условия реакции

Обработка

1. 1
   Другоеdegassed
2. 2
   Температураthe mixture is heated
3. 3
   Температураunder reflux for 20 h
4. 4
   ТемператураAfter cooling
5. 5
   Другоеthe organic phase is separated off
6. 6
   Промывкаwashed three times with 200 ml of water
7. 7
   Сушкаonce with 200 ml of saturated, aqueous sodium chloride solution, dried over magnesium sulfate
8. 8
   Другоеevaporated to dryness in vacuo in a rotary evaporator
9. 9
   ДругоеThe grey residue is recrystallised from hexane
10. 10
    ФильтрацияThe deposited crystals are filtered off with suction
11. 11
    Промывкаwashed with a little MeOH
12. 12
    Другоеsubsequently dried in vacuo

Методика

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.

Источник