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

HRID 1159822Notes

Reaction equation

HRID 1159822 reaction equation
[CH3:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[Br:12]Br>C(Cl)(Cl)Cl.CC(O)=O>[Br:12][C:7]1[CH:6]=[CH:5][C:4]([OH:8])=[C:3]([N+:9]([O-:11])=[O:10])[C:2]=1[CH3:1]

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

3-Methyl-2-nitrophenol (11.4 g, 74.4 mmol) was dissolved in chloroform (11 ml) and cooled on an ice-water bath. Bromine (3.8 ml, 74.4 mmol) in HOAc (9 ml) was added drop wise to the stirred, cooled solution. The solution was stirred at 0° for 2 h. Ice was added to the reaction mixture. The organic phase was separated and the water phase was extracted with chloroform. The combined organic phase was washed with brine and water. Evaporation gave 17.2 g. MS (ESI+) for C7H6BrNO3 m/z 232, 234 (M+H)+.

Workup

  1. temperaturecooled on an ice-water bath
  2. temperaturecooled solution
  3. additionIce was added to the reaction mixture
  4. customThe organic phase was separated
  5. extractionthe water phase was extracted with chloroform
  6. washThe combined organic phase was washed with brine and water
  7. customEvaporation
  8. customgave 17.2 g

Sources & evidence

ORD record
ord-2c38d0e48adf4f33a1c7c593559fe4e2
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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