N-2-Naphthalenylacetamide → HCID 13663774, Verbindung
Reaktionsgleichung
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)(=[O:3])[CH3:2].[F:15][B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2>CCOC(C)=O>[F:15][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[CH:14][C:5]=1[NH:4][C:1](=[O:3])[CH3:2]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of 1.95 g (10 mmol) of 2-acetylaminonaphthalene, and 7.1 g (20 mmol) of 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor®) in 30 mL of CH2CN is heated to reflux under an atmosphere of nitrogen for 24 hours. After cooling to room temperature, 50 mL of EtOAc is added and the mixture is washed with H2O and dried over MgSO4. Evaporation of the solvents gives a syrup that is purified by flash chromatography on silica gel (25% EtOAc/hexane) to give 1-fluoro-2-acetylaminonaphthalene.