Water → 5-Bromo-2-nitrophenol

HRID 1452459Notes

Reaction equation

HRID 1452459 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[N+:9]([O-])([O-:11])=[O:10].[Na+].O>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[C:4]([OH:8])[CH:3]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 115633-BromophenolHCID 24268Sodium Nitrate

Product 1

HCID 139704965-Bromo-2-nitrophenolYield 20%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

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.

Workup

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. dry with materialthe extract was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (silica gel, 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a70127fc5c2d4c6ba82ef24435d3f56c
Source dataset
uspto-grants-2009_01
Patent number
US07473686B2

Reaction notes

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