Reaction #1797507

Reaction equation

Water

3-Bromophenol

sodium nitrate

water

→

title compound

Yield 20.0%

5-bromo-2-nitrophenol

Yield 20.0%

Solvents

sulfuric acid

Conditions

Workup

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

Procedure

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