Reacción #1574

Ecuación de reacción

4'-chloro-2'-fluoroacetanilide

nitric acid

→

title product

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

Disolventes

sulfuric acid

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONpoured onto ice
2. 2
   FiltraciónThe resultant aqueous mixture is filtered
3. 3
   Otroto obtain a tan solid which
4. 4
   Lavadois washed with water
5. 5
   Otrodried overnight
6. 6
   Otrorecrystallized from a chloroform/hexanes (17:1) solution

Procedimiento

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.

Fuente