Réaction #1797507

Équation de réaction

Water

3-Bromophenol

sodium nitrate

water

→

title compound

Rendement 20.0%

5-bromo-2-nitrophenol

Rendement 20.0%

Solvants

sulfuric acid

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source