Réaction #10413

Équation de réaction

4,5-difluoroanthranilic acid

acetic acid

hypochlorous acid tert-butyl ester

→

3-chloro-4,5-difluoroanthranilic acid

Rendement 100.8%

Solvants

dichloromethane

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Lavagewashed with water and brine
2. 2
   SéchageThe organic layer is dried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated
5. 5
   AutreThe resulting residue is purified via flash column chromatography (5% isopropyl alcohol/1% formic acid/94% dichloromethane)

Mode opératoire

To a solution of 4,5-difluoroanthranilic acid (2.45 g, 14.2 mmol) in dichloromethane (25 mL) is added acetic acid (10 mL) and hypochlorous acid tert-butyl ester (1.75 mL, 15.6 mmol). After 2 hours, the reaction mixture is diluted with ethyl acetate and washed with water and brine. The organic layer is dried over MgSO4, filtered, and concentrated. The resulting residue is purified via flash column chromatography (5% isopropyl alcohol/1% formic acid/94% dichloromethane) to afford 3-chloro-4,5-difluoroanthranilic acid as an oil (2.97 g). MS CI: m/z 206 (M+).

Source