Réaction #3783

Équation de réaction

2-chloro-6-fluorophenyl acetic acid

3,5-dimethoxyphenol

potassium carbonate

→

2-(3,5-dimethoxyphenoxy)-6-fluorophenyl acetic acid

Rendement 86.1%

Solvants

N,N-Dimethylformamide

Conditions de réaction

Traitement

1. 1
   AutreThe resulting reaction solution
2. 2
   Autrewas partitioned with ethyl acetate and dilute hydrochloric acid
3. 3
   Lavagethe organic phase was washed in water and in a saturated sodium chloride solution
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONto distill off the solvents under reduced pressure
6. 6
   AutreThe residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=7:3)

Mode opératoire

N,N-Dimethylformamide (20 ml) was added to 2-chloro-6-fluorophenyl acetic acid (3.77 g), 3,5-dimethoxyphenol (3.08 g), potassium carbonate (5.52 g), copper iodide (950 mg) and copper (250 mg), for stirring at 120° C. for 20 hours. The resulting reaction solution was partitioned with ethyl acetate and dilute hydrochloric acid, and the organic phase was washed in water and in a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, to distill off the solvents under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=7:3), to recover 2-(3,5-dimethoxyphenoxy)-6-fluorophenyl acetic acid (5.27 g; yield of 86%). By 1H-NMR (90 MHz, CDCl3), the compound has the peaks shown below.

Source