Pyridine, hydrofluoride (1:1) → 1-(1,1-Dimethylethyl)-4-fluorobenzene
Reaktionsgleichung
[C:1]([C:5]1[CH:11]=[CH:10][C:8](N)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[FH:18].N([O-])=O.[Na+]>>[C:1]([C:5]1[CH:11]=[CH:10][C:8]([F:18])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]Komponenten
4
Versuchsvorschrift
In a steel bomb were combined 4-tert-butyl aniline (1 eq) and 70% hydrogen fluoride-pyridine (25 g/gm aniline). Sodium nitrite (1.5 eq) was then added portion wise over 5 minutes. The resulting solution was allowed to stir for 1 h at room temperature and then the bomb was sealed and heated at 85° C. for 1 h. Solution was then quenched with water/ice and extracted with ethyl ether. Organics washed with brine and dried with sodium sulfate and concentrated to afford 1-tert-butyl-4-fluorobenzene.