3-Methoxyphenol → 2-Bromo-5-methoxyphenol

HRID 1457596Notes

Reaction equation

HRID 1457596 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[Br:10]Br>C(=S)=S>[Br:10][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[OH:9]

Participants

4

Reactant 2

HCID 90073-MethoxyphenolHCID 24408Bromine

Product 1

HCID 134938392-Bromo-5-methoxyphenolYield 85%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a mixed solution of 25 g of 3-methoxyphenol and 100 ml of carbon disulfide (CS2) was added dropwise 10.3 ml of bromine at room temperature. After stirring the mixture for 30 minutes, the solvent was removed under reduced pressure, and water was added to the residue. The reaction mixture was extracted with diethyl ether. The extract was washed and dried, and the solvent was removed under reduced pressure to give 34.8 g of 2-bromo-5-methoxyphenol (yield: 85%, boiling point: 96°-98° C. (4 mmHg), colorless oily product).

Workup

  1. customthe solvent was removed under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionThe reaction mixture was extracted with diethyl ether
  4. washThe extract was washed
  5. customdried
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a94f5797df314f98a09dce9a57684fd9
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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