Reaktion #69517

Reaktionsgleichung

ethyl 4-amino-3-methoxybenzoate

acetonitrile

N-chlorosuccinimide

→

title compound

Ausbeute 75.4%

Ethyl 4-amino-3-chloro-5-methoxybenzoate

Ausbeute 75.4%

Lösungsmittel

n-heptane ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas returned to room temperature
2. 2
   workup.DISTILLATIONthe solvent in the mixture was distilled off under reduced pressure
3. 3
   SonstigeThe residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

Vorschrift

To ethyl 4-amino-3-methoxybenzoate (17.8 g, 91.2 mmol), were added acetonitrile (170 mL) and N-chlorosuccinimide (13.4 g, 100 mmol) in this order, and the mixture was stirred at 60° C. for two hours. The mixture was returned to room temperature, and the solvent in the mixture was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate:n-heptane/ethyl acetate=8/1 then 4/1) to obtain the title compound (158 g, 68.8 mmol).

Quelle