반응 #67474

반응 방정식

NaHCO3

1-bromo-4-fluoro-2-methyl-5-nitrobenzene

SnCl2.2H2O

→

5-bromo-2-fluoro-4-methylaniline

수율 31.9%

용매

ethanol

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도at reflux for 3 h
3. 3
   기타The solvent was evaporated under reduced pressure
4. 4
   기타to give a residue, which
5. 5
   여과The solid was filtered off
6. 6
   추출the filtrate was extracted with dichloromethane (200 mL×3)
7. 7
   건조The combined organics were dried over anhydrous Na2SO4
8. 8
   기타evaporated under reduced pressure
9. 9
   기타The residue was purified by column chromatography (petroleum ether/EtOAc=10/1)

실험 절차

To a stirred solution of 1-bromo-4-fluoro-2-methyl-5-nitrobenzene (18.0 g) in ethanol (300 mL) was added SnCl2.2H2O (51.8 g, 0.230 mol) at room temperature. The mixture was heated at reflux for 3 h. The solvent was evaporated under reduced pressure to give a residue, which was poured into ice water. The aqueous phase was basified with sat. NaHCO3 to pH 7. The solid was filtered off and the filtrate was extracted with dichloromethane (200 mL×3). The combined organics were dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography (petroleum ether/EtOAc=10/1) to afford 5-bromo-2-fluoro-4-methylaniline (5.0 g, 30% yield for two steps). 1NMR (400 MHz, CDCl3) δ 6.96 (d, J=8.8 Hz, 1H), 6.86 (d, J=11.6 Hz, 1H), 3.64 (br, 2H), 2.26 (s, 3H). MS (ESI) m/z (M+H+) 204.0.

출처