3-Methyl-2-nitrophenol → 4-Bromo-3-methyl-2-nitrophenol

HRID 1159790Notes

Reaction equation

HRID 1159790 reaction equation
[N+:1]([C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:11])([O-:3])=[O:2].[Br:12]Br>C(Cl)(Cl)Cl.C(O)(=O)C>[Br:12][C:8]1[CH:7]=[CH:6][C:5]([OH:11])=[C:4]([N+:1]([O-:3])=[O:2])[C:9]=1[CH3:10]

Participants

5

Reactant 2

HCID 210263-Methyl-2-nitrophenolHCID 24408Bromine

Product 1

HCID 130881794-Bromo-3-methyl-2-nitrophenol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

2-Nitro-3-methylphenol (10 g, 65 mmol) was dissolved in CHCl3 (10 mL) and cooled on ice. Br2 (3.2 mL, 62 mmol) was dissolved in concentrated acetic acid (7.5 mL) and added dropwise to the solution. The reaction mixture was stirred at 0 deg for 2 hrs. Ice was added and the layers were separated. The aqueous layer was extracted with CHCl3, the combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered and concentrated to give 4-bromo-3-methyl-2-nitrophenol, 15 g (99%).

Workup

  1. temperaturecooled on ice
  2. additionadded dropwise to the solution
  3. additionIce was added
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with CHCl3
  6. washthe combined organic layers were washed with H2O and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-518eb476ff95496c825cfa60a08f257e
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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