Reaction #1885003

Reaction equation

o-tolylboronic acid

4-bromo-2-nitrobiphenyl

potassium carbonate

→

2-methyl-2′-nitro-p-terphenyl

Solvents

water

THF

Conditions

Workup

1. 1
   Otherdegassed
2. 2
   Temperaturethe mixture is heated
3. 3
   Temperatureunder reflux for 17 h
4. 4
   TemperatureAfter cooling
5. 5
   Otherthe organic phase is separated off
6. 6
   Washwashed three times with 200 ml of water
7. 7
   Dryingonce with 200 ml of saturated, aqueous sodium chloride solution, dried over magnesium sulfate
8. 8
   Otherevaporated to dryness in a rotary evaporator
9. 9
   OtherThe grey residue is recrystallised from hexane
10. 10
    FiltrationThe deposited crystals are filtered off with suction
11. 11
    Washwashed with a little MeOH
12. 12
    Otherdried in vacuo

Procedure

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