2,6-Dimethoxyphenol → 4-Bromo-2,6-dimethoxyphenol

HRID 1784366Notes

Reaction equation

HRID 1784366 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]N1C(=O)CCC1=O>C(Cl)Cl>[Br:12][C:7]1[CH:6]=[C:5]([O:9][CH3:10])[C:4]([OH:11])=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

4

Reactant 2

HCID 70412,6-DimethoxyphenolHCID 67184N-bromobutanimide

Product 1

HCID 148458764-Bromo-2,6-dimethoxyphenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled (−78° C.) solution of 2,6-dimetoxyphenol (13)(15 g, 97.35 mmol) in CH2Cl2 (200 ml) was added N-bromosuccinimide (17.4 g, 97.35 mmol) portionwise over twenty minutes. The reaction mixture was stirred at −78° C. under an inert atmosphere for four hours before being allowed to warm to room temperature where it was stirred for a further 16 hours. The solvent was then removed in vacuo to give a slurry that was purified by flash chromatography (SiO2) (7:3—CH2Cl2:Hexanes) and then re-crystallised from CH3Cl/hexanes to give the title compound as a white solid that was analytically clean (9.66 g, 42.57%). m/z (LC-MS, ESP): 231 [M−H]−, R/T=3.17 mins

Workup

  1. temperatureto warm to room temperature where it
  2. stirringwas stirred for a further 16 hours
  3. customThe solvent was then removed in vacuo
  4. customto give a slurry that
  5. customwas purified by flash chromatography (SiO2) (7:3—CH2Cl2:Hexanes)
  6. customre-crystallised from CH3Cl/hexanes

Sources & evidence

ORD record
ord-066d3d069d40475f9aacc75728eab20e
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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