Reaktion #67474

Reaktionsgleichung

NaHCO3

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

SnCl2.2H2O

→

5-bromo-2-fluoro-4-methylaniline

Ausbeute 31.9%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturat reflux for 3 h
3. 3
   SonstigeThe solvent was evaporated under reduced pressure
4. 4
   Sonstigeto give a residue, which
5. 5
   FiltrationThe solid was filtered off
6. 6
   Extraktionthe filtrate was extracted with dichloromethane (200 mL×3)
7. 7
   TrocknenThe combined organics were dried over anhydrous Na2SO4
8. 8
   Sonstigeevaporated under reduced pressure
9. 9
   SonstigeThe residue was purified by column chromatography (petroleum ether/EtOAc=10/1)

Vorschrift

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.

Quelle