Ethanolamine → (RS)-1-(4-bromo-2-fluorophenyl)-2-(2-hydroxyethylamino)ethanol

反応式

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][O:9]2)=[C:4]([F:11])[CH:3]=1.[NH2:12][CH2:13][CH2:14][OH:15].CCOC(C)=O.C1COCC1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:9])[CH2:10][NH:12][CH2:13][CH2:14][OH:15])=[C:4]([F:11])[CH:3]=1

参加物

実験手順

To a stirred solution of (RS)-2-(4-bromo-2-fluorophenyl)oxirane (12.3 g) in THF (40 ml) was added 2-aminoethanol (33.9 ml) and the mixture was stirred at room temperature overnight. The reaction mixture was then poured into EtOAc/THF (3:1) and washed with saturated brine. The organic layer was separated, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel; gradient: 0% to 35% MeOH in dichloromethane containing a few drops of aq. NH3) to afford (RS)-1-(4-bromo-2-fluorophenyl)-2-(2-hydroxyethylamino)ethanol (12.0 g, 76%) as a brown oil. MS (ISP): 280.0 ([{81Br}M+H]−), 278.0 ([{79Br}M+H]+).