Réaction #5976

Équation de réaction

methyl 4-acetylamino-5chlorosalicylate

3-bromocyclohexene

K2CO3

DMF

→

methyl 2-(cyclohexen -3-yloxy)-4-acetylamino-5-chlorobenzoate

Solvants

water

Conditions de réaction

Traitement

1. 1
   Filtrationfiltered
2. 2
   Autredried
3. 3
   Extractionextracted into ether
4. 4
   workup.ADDITIONThe ether solution is treated with charcoal
5. 5
   Filtrationfiltered
6. 6
   Autreevaporated to dryness

Mode opératoire

A mixture of 2.5 g methyl 4-acetylamino-5chlorosalicylate, 2 g of 3-bromocyclohexene, 2 g K2CO3 and 30 ml DMF are combined and heated at 110° C. overnight. The reaction mixture is then poured into water, filtered, dried and then extracted into ether. The ether solution is treated with charcoal, filtered and evaporated to dryness to obtain methyl 2-(cyclohexen -3-yloxy)-4-acetylamino-5-chlorobenzoate. This is then purified by recrystallization from ether/hexane. (M.P. 100°-102° C.)

Source