Ethanol → Ethyl 4-fluoro-3-nitrobenzoate
Reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH2:14](O)[CH3:15].S(=O)(=O)(O)O>>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:14][CH3:15])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]Participants
Procedure
4-fluoro-3-nitrobenzoic acid (1 equivalent) was dissolved in ethanol (5.3 equivalents), and concentrated sulfuric acid (0.25 equivalent) was added thereto, and the resulting mixture was heated under reflux for 5 hours. After cooling the reaction mixture, the reaction mixture was concentrated under reduced pressure until the volume was reduced to about half the initial value. The resulting mixture was then neutralized by adding sodium carbonate and was subjected to extraction with ether three times. The obtained extracted liquid was washed with saturated brine and then with water, and the ether layer was dried over anhydrous sodium sulfate. The resulting layer was then evaporated to dryness under reduced pressure, whereby ethyl 4-fluoro-3-nitrobenzoate was obtained.
Workup
- temperaturethe resulting mixture was heated
- temperatureunder reflux for 5 hours
- temperatureAfter cooling the reaction mixture
- concentrationthe reaction mixture was concentrated under reduced pressure until the volume
- additionby adding sodium carbonate
- extractionwas subjected to extraction with ether three times
- extractionThe obtained extracted liquid
- washwas washed with saturated brine
- dry with materialwith water, and the ether layer was dried over anhydrous sodium sulfate
- customThe resulting layer was then evaporated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-3d407c849866443cbee43fda9d7ce9e0
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08053461B2
Reaction notes
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