Water → 6-Bromo-7-methoxy-2,2-dimethyl-chroman-4-one

HRID 2180454Notes

Reaction equation

HRID 2180454 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][C:7]([CH3:14])([CH3:13])[CH2:6][C:5]2=[O:15].[C:16](=O)([O-])[O-].[K+].[K+].IC.O>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:16])[O:8][C:7]([CH3:13])([CH3:14])[CH2:6][C:5]2=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 224908286-Bromo-7-hydroxy-2,2-dimethyl-chroman-4-one2×

Product 1

HCID 134522776-Bromo-7-methoxy-2,2-dimethyl-chroman-4-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 6-bromo-7-hydroxy-2,2-dimethyl-chroman-4-one (Compound 3, 2.00 g, 7.4 mmol) in acetone (100 mL) were added potassium carbonate (500 mg) and iodomethane (5.22 g, 36.8 mmol). The mixture was then heated to reflux for 2 h. After cooling to room temperature, water was added to the mixture until all solids dissolved. The resulting solution was then extracted with diethyl ether, washed with brine, dried (MgSO4) and concentrated at reduced pressure to give a yellow residue. Purification by flash chromatography (silica gel, 95:5 hexane/ethyl acetate) gained the title compound as a white solid.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 2 h
  3. dissolutiondissolved
  4. extractionThe resulting solution was then extracted with diethyl ether
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated at reduced pressure
  8. customto give a yellow residue
  9. customPurification by flash chromatography (silica gel, 95:5 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a95aef98196f41d49d3dbbc20e4dc96e
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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