Reaction #1885005

Reaction equation

1-naphthylboronic acid

4-bromo-2-nitrobiphenyl

potassium carbonate

→

4-naphth-1-yl-2-nitrobiphenyl

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 400 ml of water
7. 7
   Dryingonce with 400 ml of saturated, aqueous sodium chloride solution, dried over magnesium sulfate
8. 8
   Otherevaporated to dryness in vacuo 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

1.62 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.

Source