Acetic Acid → 3-(Difluoromethyl)aniline
Reaction equation
C(O)(=O)C.[F:5][CH:6]([F:16])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1>[Fe].C(OCC)(=O)C>[F:5][CH:6]([F:16])[C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=1)[NH2:13]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
100 mg of Fe was added intio 3 ml of acetic acid and refluxed for 15 minutes. After lowering the temperature into room temperature, the mixture was added with 1-(difluoromethyl)-3-nitrobenzene (0.2 g, 1.15 mmol) and refluxed again for 1 hour. After addition of 20 ml ethyl acetate, impurities were removed using cellite and the organic layer was concentrated under vacuum. After column chromatography (ethylacetate/n-hexane, 1/15), the title compound (0.16 g, 50%) was obtained.
Workup
- temperaturerefluxed for 15 minutes
- custominto room temperature
- temperaturerefluxed again for 1 hour
- customwere removed
- concentrationthe organic layer was concentrated under vacuum
Sources & evidence
- ORD record
- ord-21e40ba58272410b983caa869b7450ac
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09062066B2
Reaction notes
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