Reaktion #157996

Reaktionsgleichung

phosphoryl bromide

2-Cyano-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]-quinoline-6-carboxamide-1-oxide

sodium hydrogen carbonate

→

4-bromo-2-cyano-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]quinoline-6-carboxamide

Ausbeute 43.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   ExtraktionAfter extracting the mixture twice with ethyl acetate
3. 3
   Waschenwashed with water
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   FiltrationThe drying agent was filtered off
6. 6
   Sonstigethe solvent was removed by distillation under the reduced pressure
7. 7
   SonstigeThe resulting residues were purified by column chromatography

Vorschrift

2-Cyano-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]-quinoline-6-carboxamide-1-oxide (96 mg) was dissolved in acetonitrile, added with phosphoryl bromide (250 mg), and stirred at 100° C. for 5 hours. After cooling to room temperature, the reaction solution was poured into ice water and neutralized with sodium hydrogen carbonate. After extracting the mixture twice with ethyl acetate, the organic phases were combined and washed with water, and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the solvent was removed by distillation under the reduced pressure. The resulting residues were purified by column chromatography to obtain 4-bromo-2-cyano-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]quinoline-6-carboxamide (46 mg, 43%).

Quelle