Reacción #50769

Ecuación de reacción

2-fluoronitrobenzene

4-iodoaniline

triethylamine

→

N-(4-iodophenyl)-2-nitroaniline

Rendimiento 48.2%

Disolventes

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaunder reflux
3. 3
   Temperaturato cool
4. 4
   LavadoThe solution was washed with water (2×100 ml), aqueous 2M potassium hydroxide (100 ml) and brine (100 ml)
5. 5
   SecadoThe organics were dried over anhydrous magnesium sulphate
6. 6
   Otrothe solvent removed under reduced pressure
7. 7
   Otroto give an orange solid
8. 8
   OtroRecrystalisation from ethyl acetate

Procedimiento

A mixture of 2-fluoronitrobenzene (14 g, 100 mmol), 4-iodoaniline (11 g, 50 mmol) and triethylamine (14 ml, 100 mmol) was heated under reflux. After 48 h the reaction mixture was allowed to cool and ethyl acetate (300 ml) was added. The solution was washed with water (2×100 ml), aqueous 2M potassium hydroxide (100 ml) and brine (100 ml). The organics were dried over anhydrous magnesium sulphate and the solvent removed under reduced pressure to give an orange solid. Recrystalisation from ethyl acetate gave N-(4-iodophenyl)-2-nitroaniline (8.2 g, 48%) as an orange crystalline solid. deltaH (250 MHz, CDCl3) 9.39 (1H, s), 8.21 (1H, dd, J 8.5, 1.5 Hz), 7.71 (2H, dd, J 8.6, 2.0 Hz), 7.39 (1H, m), 7.24 (1H, m), 7.05 (2H, dd, J 8.6, 1.4 Hz), 6.83 (1H, m).

Fuente