Water → 1-(4-Bromo-2-methoxyphenyl)ethan-1-one

HRID 2086678Notes

Reaction equation

HRID 2086678 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([OH:11])[CH:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 107274031-(4-Bromo-2-hydroxyphenyl)ethan-1-one

Product 1

HCID 112184481-(4-Bromo-2-methoxyphenyl)ethan-1-oneYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-(4-bromo-2-hydroxyphenyl)-1-ethanone (28.8 g, 134 mmol), potassium carbonate (48.6 g, 352 mmol) in DMF (63 ml) was added methyl iodide (25 g, 176 mmol), and the mixture was stirred for 20 hours. The mixture was poured into water. The whole was extracted with diethylether. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was used for next reaction without purification. (31.5 g, 99% yield).

Workup

  1. extractionThe whole was extracted with diethylether
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was used for next reaction without purification

Sources & evidence

ORD record
ord-59ab71f8371b45dab75513206edb9748
Source dataset
uspto-grants-2004_04
Patent number
US06727238B2

Reaction notes

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