Nitric Acid → 3-Bromo-4-nitrophenol

HRID 1950116Notes

Reaction equation

HRID 1950116 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[N+:9]([O-:12])([OH:11])=[O:10]>C(Cl)(Cl)Cl.C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][C:7]=1[N+:9]([O-:11])=[O:10].[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:9]([O-:12])=[O:10])=[C:4]([OH:8])[CH:3]=1

Participants

6

Reactant 2

HCID 944Nitric AcidHCID 115633-Bromophenol

Product 2

HCID 216473-Bromo-4-nitrophenolHCID 139704965-Bromo-2-nitrophenol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 3-bromophenol (10 g) in chloroform (50 ml) and acetic acid (50 ml) was added 70% nitric acid (60 ml) dropwise on an ice bath, and the solution was stirred for 1 hour. The reaction mixture was poured into ice water, extracted with ethyl acetate, then sequentially washed with a saturated aqueous solution of sodium bicarbonate, water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (4.1 g) and 5-bromo-2-nitrophenol (1.8 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washsequentially washed with a saturated aqueous solution of sodium bicarbonate, water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-d59f0f2c6e274d50bb31912e01dd555b
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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