Reaktion #1580

Reaktionsgleichung

water ethyl acetate

4-chloro-2-fluoroaniline

3,4,5,6-tetrahydrophthalic anhydride

ethyl acetate

4-chloro-2-fluoroaniline

→

title product

Ausbeute 69.3%

N-(4-Chloro-2-fluorophenyl)-1-cyclohexene-1,2-dicarboximide

Ausbeute 69.3%

Lösungsmittel

—

hexanes

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis refluxed for 2 hours
2. 2
   Temperaturrefluxed for 90 minutes
3. 3
   WaschenThe organic phase is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Einengenconcentrated in vacuo
6. 6
   Sonstigeto obtain a purple oil

Vorschrift

A mixture of 4-chloro-2-fluoroaniline (19.0 g, 130.6 mmol), and 3,4,5,6-tetrahydrophthalic anhydride (19.85 g, 130.6 mmol) in acetic acid (150 mL) is refluxed for 2 hours, treated with additional 4-chloro-2-fluoroaniline (3.0 g), refluxed for 90 minutes, stirred at room temperature overnight and poured into a water/ethyl acetate mixture. The organic phase is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a purple oil. Flash column chromatography of the oil using silica gel and 15% to 20% ethyl acetate in hexanes solutions gives the title product as an off-white solid (25.3 g, mp 81°-82° C.).

Quelle