Acetic Acid → 2-Bromo-4-nitrophenol

HRID 1106878Notes

Reaction equation

HRID 1106878 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O)(=O)C.[Br:15]Br>O>[Br:15][C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[OH:10]

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 9804-NitrophenolHCID 24408Bromine

Product 1

HCID 221092-Bromo-4-nitrophenolYield 170.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Nitrophenol (5 g, 35.9 mmol) was added to acetic acid (20 ml) and to the mixture, there was slowly added a solution of a mixture of bromine (0.93 ml, 18 mmol) and acetic acid (5 ml) at 85° C. The reaction mixture was stirred at the same temperature for 5 h and, thereafter, it was added to water and subjected to extraction with ethyl acetate. The organic extract was concentrated and the residue was subjected to column chromatography using a 7:3:1 solvent system of cyclohexane, ethyl acetate and methanol as an eluent to yield the end compound 2-bromo-4-nitrophenol (6.7 g).

Workup

  1. additionwas slowly added
  2. extractionsubjected to extraction with ethyl acetate
  3. extractionThe organic extract
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-349d1a3063c54a15bfe371c28373a20f
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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