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

HRID 485650Notes

Reaction equation

HRID 485650 reaction equation
[CH:1]1[C:6]([C:7]([CH2:9]O)=[O:8])=[CH:5][CH:4]=[C:3]([F:11])[CH:2]=1.CI.[H-].[Na+].CN(C)[CH:18]=[O:19]>>[CH3:9][C:7]([C:6]1[CH:5]=[CH:4][C:3]([F:11])=[CH:2][C:1]=1[O:19][CH3:18])=[O:8]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 28107151-(4-Fluorophenyl)-2-hydroxyethanone

Product 1

HCID 1428871-(4-Fluoro-2-methoxyphenyl)ethan-1-one

Conditions

Temperature
0 °C

Procedure

To a solution of 13.9 g. of 2-hydroxy-4-fluoroacetophenone and 75 ml. of dried dimethylformamide were added 30 ml. of methyl iodide. The solution was cooled to 0° C. and 4.1 g. of a 50% oil dispersion of sodium hydride were carefully added. After stirring for 1 hour at 0° C., the reaction was extracted with ethyl acetate. The organic extract was washed three times with 200 ml. each of 1N hydrochloric acid. The ethyl acetate solution was then dried and removed in vacuo. This reaction and a subsequent identical reaction provided a total of 28 g. of 2-methoxy-4-fluoroacetophenone as an oil which was used in the subsequent step without further purification.

Workup

  1. extractionthe reaction was extracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed three times with 200 ml
  4. dry with materialThe ethyl acetate solution was then dried
  5. customremoved in vacuo
  6. customThis reaction
  7. customa subsequent identical reaction
  8. customprovided a total of 28 g
  9. customof 2-methoxy-4-fluoroacetophenone as an oil which was used in the subsequent step without further purification

Sources & evidence

ORD record
ord-a588702a7a2b44dbb8434fe6ee380e94
Source dataset
uspto-grants-1985_08
Patent number
US04537889

Reaction notes

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