Water → 3-Amino-1-(3-bromophenyl)butan-2-ol

Reaktionsgleichung

[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([OH:15])[CH:10]([N+:12]([O-])=O)[CH3:11])[CH:5]=[CH:6][CH:7]=1.O>CCO.[Fe]>[NH2:12][CH:10]([CH3:11])[CH:9]([OH:15])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Komponenten

Versuchsvorschrift

To a solution of 1-(3-bromophenyl)-3-nitrobutan-2-ol (1.0 g, 3.6 mmol) in EtOH (20 mL)/H2O (1 mL), iron powder (2.0 g, 36 mmol) was added in one portion. The suspension was refluxed overnight, cooled to RT, and filtered. The filtrate was evaporated, diluted with H2O (30 mL), and extracted with EtOAc (50 mL×3). The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography (Petroleum ether:EtOAc=3:1) to afford 3-amino-1-(3-bromophenyl)butan-2-ol (600 mg, 68%). MS (ES+) C10H14BrNO requires: 243, 245 found: 244, 246[M+2+H]+(1:1).