3,5-Dimethylphenol → 2-BroMo-3,5-diMethylphenol

HRID 1787134Notes

Reaction equation

HRID 1787134 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Br:10]N1C(=O)CCC1=O>C(=S)=S>[Br:10][C:3]1[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][C:4]=1[OH:9]

Participants

4

Reactant 2

HCID 79483,5-DimethylphenolHCID 67184N-bromobutanimide

Product 1

HCID 183799822-BroMo-3,5-diMethylphenolYield 66%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of 3,5-dimethylphenol (15.0 g, 123 mmol) in carbon disulfide (330 mL) was slowly added N-bromosuccinimide (21.9 g, 123 mmol) in several batches with ice-cooling, and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure, and the precipitated crystals were filtered and then were washed with ethyl acetate-hexane (10:1). The solution was concentrated, and the residue was purified by silica gel chromatography (ethyl-acetate:hexane=1:9) to obtain 16.3 g (yield 66%) of the title compound. Oily matter.

Workup

  1. temperaturecooling
  2. distillationThe solvent was distilled off under reduced pressure
  3. filtrationthe precipitated crystals were filtered
  4. washwere washed with ethyl acetate-hexane (10:1)
  5. concentrationThe solution was concentrated
  6. customthe residue was purified by silica gel chromatography (ethyl-acetate:hexane=1:9)

Sources & evidence

ORD record
ord-3ee0d8a924914801b3fbf562509f919b
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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