Réaction #3680

Équation de réaction

ethyl 4-aminobenzoate

N-chlorosuccinimide

→

ethyl 3-chloro-4-aminobenzoate

Rendement 73.9%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Températureis refluxed overnight
2. 2
   LavageThe mixture is washed with saturated NaHCO3 solution
3. 3
   Séchagedried (Na2SO4)
4. 4
   Lavagethe filter cake washed with dichloromethane
5. 5
   ConcentrationThe filtrate is concentrated
6. 6
   workup.ADDITIONhexane added
7. 7
   TempératureChilling

Mode opératoire

A mixture of 8.26 g of ethyl 4-aminobenzoate, 8.26 g of N-chlorosuccinimide in 50 ml of dichloromethane is refluxed overnight. The mixture is washed with saturated NaHCO3 solution and dried (Na2SO4). The solution is passed through a thin pad of hydrous magnesium silicate and the filter cake washed with dichloromethane. The filtrate is concentrated and hexane added. Chilling gives 7.38 g of ethyl 3-chloro-4-aminobenzoate, m.p. 82°-83° C.

Source