2,6-Dimethoxyphenol → 3-Bromo-2,6-dimethoxyphenol

HRID 2171140Notes

Reaction equation

HRID 2171140 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[OH:11].[Br:12]Br>C(Cl)(Cl)(Cl)Cl>[Br:12][C:8]1[C:3]([O:2][CH3:1])=[C:4]([OH:11])[C:5]([O:9][CH3:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70412,6-DimethoxyphenolHCID 24408Bromine

Product 1

HCID 150736683-Bromo-2,6-dimethoxyphenolYield 66.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a stirring solution of 2,6-dimethoxy-phenol (2 g, 12.98 mmol) in CCl4 (70 mL) at −10° C. was added bromine (2.07 g, 12.98 mmol) and stirred for 2 h. The reaction mixture was diluted with CCl4, washed with water and the combined CCl4 layers were washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 3-Bromo-2,6-dimethoxy-phenol as a solid (2 g, 66%).

Workup

  1. washwashed with water
  2. washthe combined CCl4 layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e438f28456f4df9b63781dbf318c234
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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