Reaction #586157

Reaction equation

2,4-dichlorophenylboronic acid

3-iodoaniline

sodium carbonate

toluene

→

3-(2,4-dichlorophenyl)aniline

Yield 36.3%

Solvents

water

ethanol

Conditions

Workup

1. 1
   Temperatureunder reflux
2. 2
   Temperaturewith heating for 2 hours
3. 3
   workup.ADDITIONThe reaction mixture was poured into ice-cold water
4. 4
   Extractionextracted with toluene
5. 5
   WashThe toluene layer was washed with water twice
6. 6
   Dryingdried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure

Procedure

2.0 g (10.4 mmol) of 2,4-dichlorophenylboronic acid, 2.4 g (11.0 mmol) of 3-iodoaniline, 3.2 g (30.0 mmol) of sodium carbonate and 1.6 g (1.4 mmol) of tetrakis(triphenylphosphine) palladium were added to a solvent mixture of 70 ml of toluene, 30 ml of ethanol and 30 ml of water, and the reaction was carried out under reflux with heating for 2 hours. The reaction mixture was poured into ice-cold water and extracted with toluene. The toluene layer was washed with water twice and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.9 g of 3-(2,4-dichlorophenyl)aniline (yield 36.0%), which was used in Example 9 as the starting material.

Source