Reaktion #1797507

Reaktionsgleichung

Water

3-Bromophenol

sodium nitrate

water

→

title compound

Ausbeute 20.0%

5-bromo-2-nitrophenol

Ausbeute 20.0%

Lösungsmittel

sulfuric acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe resulting mixture was extracted with diethyl ether
2. 2
   Trocknenthe extract was dried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe residue was purified by flash chromatography (silica gel, 10% ethyl acetate/hexanes)

Vorschrift

3-Bromophenol (32.9 g, 0.19 mol) was added slowly to a cold (10° C.) solution of sodium nitrate (29.0 g, 0.34 mol) in conc. sulfuric acid; (40.0 g) and water (70.0 mL) and the resulting mixture was allowed to stir at room temperature for 2 h. Water (200 mL) was added and the resulting mixture was extracted with diethyl ether and the extract was dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (silica gel, 10% ethyl acetate/hexanes) to afford first the title compound (8.1 g, 20%), mp 40-42° C., then the undesired isomer, 3-bromo-4-nitrophenol, as a yellow solid (12.7 g, 31%). mp 125-127° C.

Quelle