Benzenamine, 3-bromo-4-methyl- → 3-Bromo-4-methylphenol

HRID 584284Notes

Reaction equation

HRID 584284 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](N)[CH:5]=[CH:4][C:3]=1[CH3:9].N([O-])=[O:11].[Na+]>S(=O)(=O)(O)O.O>[Br:1][C:2]1[CH:7]=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 2

HCID 82187Benzenamine, 3-bromo-4-methyl-HCID 23668193Sodium Nitrite

Product 1

HCID 103079133-Bromo-4-methylphenolYield 48.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

25 g (134 mmol) of 2-bromo-4-aminotoluene are placed in 400 ml of 1M sulfuric acid in a round-bottomed flask, and the mixture is then cooled to 0° C. 13 g (190 mmol) of sodium nitrite dissolved in 30 ml of water are added, followed by addition of 21 ml of concentrated sulfuric acid. The mixture is refluxed for 4 hours. It is then extracted with ethyl ether. The organic phase is dried over magnesium sulfate, filtered and then evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (90/10) to give 12.1 g (48%) of the expected product in the form of a brown oil.

Workup

  1. additionare added
  2. temperatureThe mixture is refluxed for 4 hours
  3. extractionIt is then extracted with ethyl ether
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with a mixture of heptane and ethyl acetate (90/10)

Sources & evidence

ORD record
ord-42292f90ca9e49e6bdd5f6d83dd85d6a
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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