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

HRID 2278393Notes

Reaction equation

HRID 2278393 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

Conditions

Temperature
0 °C

Procedure

To a solution of 3-methyl-2-nitro-phenol (20 g, 0.13 mol) in CHCl3 (20 mL) was added a solution of Br2 (6.4 mL) in HOAc (15 mL) dropwise at 0° C. and the mixture was stirred at 0° C. for 3 h. Ice was added and the mixture was extracted with CHCl3. After drying over Na2SO4, CHCl3 was removed to give 4-bromo-3-methyl-2-nitro-phenol (30 g) which was used without further purification.

Workup

  1. additionIce was added
  2. extractionthe mixture was extracted with CHCl3
  3. dry with materialAfter drying over Na2SO4, CHCl3
  4. customwas removed

Sources & evidence

ORD record
ord-bcd2ca9620634e60baec6b04a48e757e
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

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