반응 #50769

반응 방정식

2-fluoronitrobenzene

4-iodoaniline

triethylamine

→

N-(4-iodophenyl)-2-nitroaniline

수율 48.2%

용매

ethyl acetate

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도under reflux
3. 3
   온도to cool
4. 4
   세척The solution was washed with water (2×100 ml), aqueous 2M potassium hydroxide (100 ml) and brine (100 ml)
5. 5
   건조The organics were dried over anhydrous magnesium sulphate
6. 6
   기타the solvent removed under reduced pressure
7. 7
   기타to give an orange solid
8. 8
   기타Recrystalisation from ethyl acetate

실험 절차

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).

출처