Réaction #80701

Équation de réaction

4'-chloro-2'-fluoroacetanilide

nitric acid

→

title product

4'-Chloro-2'-fluoro-5'-nitroacetanilide

Solvants

sulfuric acid

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONpoured onto ice
2. 2
   FiltrationThe resultant aqueous mixture is filtered
3. 3
   Autreto obtain a tan solid which
4. 4
   Lavageis washed with water
5. 5
   Autredried overnight
6. 6
   Autrerecrystallized from a chloroform/hexanes (17:1) solution

Mode opératoire

A mixture of 4'-chloro-2'-fluoroacetanilide (51 g, 0.272 mol) in concentrated sulfuric acid (100 mL) is cooled to 0° C., treated with nitric acid (90% real, 14 mL, 0.300 mol) over 45 minutes, stirred for 10 minutes, and poured onto ice. The resultant aqueous mixture is filtered to obtain a tan solid which is washed with water, dried overnight, and recrystallized from a chloroform/hexanes (17:1) solution to give the title product as a yellow solid.

Source