Réaction #608940

Équation de réaction

NaOH

2-bromo-4-chloro-pyridine

methyl-3-hydroxybenzoate

cesium carbonate

→

3-(2-bromo-pyridin-4-yloxy)-benzoic acid

Solvants

ethyl acetate

MeOH

water

DMSO

Conditions de réaction

Traitement

1. 1
   Lavagewashed with brine (3×50 ml)
2. 2
   Séchagedried over Na2SO4
3. 3
   Autreevaporated
4. 4
   Autreto give a colorless oil
5. 5
   TempératureThe mixture was heated at 60° C. for 20 minutes
6. 6
   FiltrationThe precipitates were filtered
7. 7
   Lavagewashed with water
8. 8
   Autredried in vacuo

Mode opératoire

A mixture of 2-bromo-4-chloro-pyridine (200 mg, 1.04 mmol), methyl-3-hydroxybenzoate (158 mg, 1.04 mmol), cesium carbonate (507 mg, 1.56 mmol) in 10 ml of anhydrous DMSO was heated at 66° C. for 5 hours. The mixture was diluted with ethyl acetate (100 ml), washed with brine (3×50 ml), dried over Na2SO4 and evaporated to give a colorless oil. The oil was dissolved in MeOH (8 ml), and 2M NaOH solution (4 ml, 8 mmol) was added. The mixture was heated at 60° C. for 20 minutes, poured into 50 ml of water, and acidified to pH=4. The precipitates were filtered, washed with water and dried in vacuo to give 3-(2-bromo-pyridin-4-yloxy)-benzoic acid as white solid. Yield: 170 mg, 56%.

Source