(E)-1-(4-bromo-2-nitrostyryl)pyrrolidine → 4-Bromo-2-nitrobenzaldehyde
反応式
I([O-])(=O)(=O)=[O:2].[Na+].[Br:7][C:8]1[CH:20]=[CH:19][C:11](/[CH:12]=C/N2CCCC2)=[C:10]([N+:21]([O-:23])=[O:22])[CH:9]=1>C1COCC1.O>[Br:7][C:8]1[CH:20]=[CH:19][C:11]([CH:12]=[O:2])=[C:10]([N+:21]([O-:23])=[O:22])[CH:9]=1参加物
4
実験手順
To a solution of sodium periodate (298 g, 1.40 mol) in THF—H2O (4 L, 1:1) at 0° C. was added (E)-1-(4-bromo-2-nitrostyryl)pyrrolidine (138 g, 464 mmol). The mixture was stirred for 15 h and then filtered to remove solid precipitates. The aqueous layer from the filtrate was separated and extracted with EtOAc (4×200 mL). The combined organic layers were washed with H2O (2×200 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude product that was purified by silica gel flash column chromatography (5% EtOAc in hexanes) to afford 91 g (86%) of 4-bromo-2-nitrobenzaldehyde.