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

HRID 550166Notes

Reaction equation

HRID 550166 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(O)(=O)C>[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

4

Reactant 2

HCID 210263-Methyl-2-nitrophenolHCID 24408Bromine

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-methyl-2-nitrophenol (2.0 g, 13.06 mmol) in acetic acid (40 mL) was added bromine (0.70 mL, 13.71 mmol) and the mixture was stirred at RT for 5 h. The reaction was poured in to ice water and the yellow precipitate formed was filtered and washed with water and dried in vacua to yield 4-bromo-3-methyl-2-ninophenol. 1H NMR. (400 MHz, CDCl3) δ=2.61 (s, 3H), 2.62 (s, 5H), 6.92 (d, J=8.84 Hz, 1H), 7.66 (d, J=9.09 Hz, 1H) and 9.28 (s, 1 H); MS (ES+): m/z 215.00 [M-17].

Workup

  1. customthe yellow precipitate formed
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried in vacua
  5. customto yield 4-bromo-3-methyl-2-ninophenol

Sources & evidence

ORD record
ord-69d0cda822bf4a82b700a03d084273f2
Source dataset
uspto-grants-2011_05
Patent number
US07943767B2

Reaction notes

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