Nitrobenzene → 3-(4-Fluorophenyl)-2,1-benzisoxazole

Reaktionsgleichung

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#N)=[CH:4][CH:3]=1.[OH-].[Na+].[N+:13]([C:16]1C=[CH:20][CH:19]=[CH:18][CH:17]=1)([O-])=[O:14]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:14][N:13]=[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:9]=23)=[CH:6][CH:7]=1

Komponenten

Versuchsvorschrift

A total of 50.7 g (0.375 mol) of 4-fluorophenyl-acetonitrile is slowly added to a vigorously stirred, room-temperature solution of 150 g (3.75 mol) of sodium hydroxide in 750 ml of absolute methanol. After solution is complete, 46 g (0.374 mol) of nitrobenzene is slowly added. The resulting solution is warmed to 65°-70° C. and held at this temperature for 9 hours. The dark slurry is cooled to room temperature, diluted with 250 ml of 50% methanol, and cooled in an ice bath. The resulting dark precipitate is filtered and washed with cold methanol until the methanol washings were clear. The product (16) is recrystallized from toluene.