Reaction #77697

Reaction equation

2-amino-5-bromobenzonitrile

phenylboronic acid

potassium carbonate

→

desired compound

Yield 91.6%

2-Amino-4-phenylbenzonitrile

Yield 91.6%

Solvents

dimethoxyethane water

water

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureat reflux for 4 hours
3. 3
   Extractionextracted with ethyl acetate
4. 4
   OtherThe organic phase was dried
5. 5
   Othersolvent evaporated

Procedure

A mixture of 2-amino-5-bromobenzonitrile (1.0 g, 5 mmol), phenylboronic acid (0.92 g, 7.5 mmol), tetrakis(triphenylphosphine)palladium (50 mg) and potassium carbonate (3.5 g, 25 mmol) in dimethoxyethane/water 2:1 (60 mL) was heated at reflux for 4 hours. After cooling to room temperature the reaction was diluted with water and extracted with ethyl acetate. The organic phase was dried and solvent evaporated. Trituation with petroleum ether gave 0.89 g of the desired compound.

Source