Reaction #10413

Reaction equation

4,5-difluoroanthranilic acid

acetic acid

hypochlorous acid tert-butyl ester

→

3-chloro-4,5-difluoroanthranilic acid

Yield 100.8%

Solvents

dichloromethane

ethyl acetate

Conditions

Workup

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

Procedure

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