Ethyl Acetate → 5-Bromo-2-morpholin-4-ylaniline
Reaktionsgleichung
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[C:4]([N+:14]([O-])=O)[CH:3]=1.CCOC(C)=O.[Sn](Cl)Cl>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)=[C:4]([CH:3]=1)[NH2:14]Komponenten
4
Versuchsvorschrift
To a solution of 4-(4-bromo-2-nitrophenyl)morpholine (13.2 g, 46 mmol) dissolved in EtOAc (200.00 mL, 2043 mmol) at rt was added all in one portion tin(II) chloride dehydrate (52 g, 230 mmol). An exotherm developed and the orange color faded to a faint yellow. The reaction was stirred at ambient temperature for 15 min then heated to reflux for 45 min. After 60 min TLC indicated no starting material remained and the reaction was equilibrated to rt. The reaction was washed with 200 mL 5N aq. Sodium hydroxide solution followed by 100 mL water and 50 mL brine. The organic separation was stirred over anhydrous magnesium sulfate, filtered and the filtrate concd under reduced pressure to afford a pale yellow solid. Mass Spectrum (ESI) m/e=257.0 & 259.0 (M+1).