Dimethylformamide → 1-(4-Fluoro-2-methoxyphenyl)ethan-1-one
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
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 13.9 g. of 2-hydroxy-4-fluoroacetophenone in 75 ml. of dry 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 one 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
- extractionthe reaction was extracted with ethyl acetate
- extractionThe organic extract
- washwas washed three times with 200 ml
- dry with materialThe ethyl acetate solution was then dried
- customremoved in vacuo
- customThis reaction
- customa subsequent identical reaction
- customprovided a total of 28 g
- customof 2-methoxy-4-fluoroacetophenone as an oil which was used in the subsequent step without further purification
Sources & evidence
- ORD record
- ord-acd80b216dae4ab58335d760541d5e06
- Source dataset
- uspto-grants-1987_06
- Patent number
- US04670445
Reaction notes
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