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

HRID 1872842Notes

Reaction equation

HRID 1872842 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[OH:11])=[O:3].CI.[C:14](=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[O:11][CH3:14])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27373264'-Fluoro-2'-hydroxyacetophenone

Product 1

HCID 1428871-(4-Fluoro-2-methoxyphenyl)ethan-1-oneYield 100.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-fluoro-2-hydroxyacetophenone (1 g, 6.5 mmol), methyl iodide (0.4 ml), potassium carbonate (1.34 g, 9.7 mmol) in anhydrous dimethylsulfoxide (20 ml) was allowed to stir at room temperature for 2 hours. The mixture was poured into water (100 ml) and extracted with methylene chloride (3×100 ml). The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum to afford 1.1 g (100%) of product as a light yellow solid: mp 50-51.5° C.

Workup

  1. extractionextracted with methylene chloride (3×100 ml)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-bcbfe6cf82a648c18a1e5d501a46dffa
Source dataset
uspto-grants-2000_08
Patent number
US06110956

Reaction notes

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