Réaction #1885003

Équation de réaction

o-tolylboronic acid

4-bromo-2-nitrobiphenyl

potassium carbonate

→

2-methyl-2′-nitro-p-terphenyl

Solvants

water

THF

Conditions de réaction

Traitement

1. 1
   Autredegassed
2. 2
   Températurethe mixture is heated
3. 3
   Températureunder reflux for 17 h
4. 4
   TempératureAfter cooling
5. 5
   Autrethe organic phase is separated off
6. 6
   Lavagewashed three times with 200 ml of water
7. 7
   Séchageonce with 200 ml of saturated, aqueous sodium chloride solution, dried over magnesium sulfate
8. 8
   Autreevaporated to dryness in a rotary evaporator
9. 9
   AutreThe grey residue is recrystallised from hexane
10. 10
    FiltrationThe deposited crystals are filtered off with suction
11. 11
    Lavagewashed with a little MeOH
12. 12
    Autredried in vacuo

Mode opératoire

1.7 g (1.49 mmol) of Pd(PPh3)4 are added to a well-stirred, degassed suspension of 25 g (183.8 mmol) of o-tolylboronic acid, 51.1 g (183.8 mmol) of 4-bromo-2-nitrobiphenyl and 66.5 g (212.7 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 17 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 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: 50.5 g, 95% of theory; purity: 99.5% according to HPLC.

Source