3-Bromo-o-toluidine → 3-Bromo-2-methylphenol

HRID 2307552Notes

Reaction equation

HRID 2307552 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[C:4](N)[CH:5]=[CH:6][CH:7]=1.N([O-])=[O:11].[Na+]>S(=O)(=O)(O)O.O>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([OH:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 1235383-Bromo-o-toluidineHCID 23668193Sodium Nitrite

Product 1

HCID 111714303-Bromo-2-methylphenol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

20 g (107 mmol) of 3-bromo-2-methylphenylamine are dissolved in 150 mL of aqueous 1.0M sulphuric acid and the mixture is cooled to 0° C. A solution of 8.9 g (129 mmol) of sodium nitrite in 20 mL of water is added slowly. The medium is stirred for 15 minutes at 0° C., and 50 mL of concentrated sulphuric acid are then added. The reaction medium is then heated at 100° C. for 1 hour and then cooled and diluted in water. After extraction with ethyl ether, the residue obtained is recrystallized from a heptane/dichloromethane mixture. A yellow solid is obtained (m.p.=89° C.; m=12.3 g; Y=61%).

Workup

  1. temperatureThe reaction medium is then heated at 100° C. for 1 hour
  2. temperaturecooled
  3. extractionAfter extraction with ethyl ether
  4. customthe residue obtained
  5. customis recrystallized from a heptane/dichloromethane mixture
  6. customA yellow solid is obtained (m.p.=89° C.; m=12.3 g; Y=61%)

Sources & evidence

ORD record
ord-e7d958081435457a936b1e291eba1e56
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Reaction notes

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