Carbon Disulfide → 5-Bromo-2,4-dimethoxyphenol

HRID 1457594Notes

Reaction equation

HRID 1457594 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[OH:11].C(=S)=S.[Br:15]Br>O>[Br:15][C:6]1[CH:5]=[C:4]([OH:11])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 24408BromineHCID 5930062,4-Dimethoxyphenol

Product 1

HCID 220994575-Bromo-2,4-dimethoxyphenolYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed solution comprising 8.6 g of 2,4-dimethoxyphenol and 80 ml of carbon disulfide (CS2) was added dropwise 2.86 ml of bromine at 10° to 15° C. After stirring the mixture at room temperature for one hour, water was added to the reaction mixture and the reaction mixture was extracted with diethyl ether. The extract was washed and dried, and the solvent was removed under reduced pressure. Hexane was added to the obtained residue and the precipitated crystals were collected by filtration to give 12.0 g of 3-bromo-4,6-dimethoxyphenol (yield: 92%, melting point: 78°-80° C.).

Workup

  1. extractionthe reaction mixture was extracted with diethyl ether
  2. washThe extract was washed
  3. customdried
  4. customthe solvent was removed under reduced pressure
  5. additionHexane was added to the obtained residue
  6. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-019c909aa59c45e6912ff3b83990ce73
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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