Acetic Acid → 3-(Difluoromethyl)aniline

HRID 2175381Notes

Reaction equation

HRID 2175381 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

HCID 176Acetic AcidHCID 214079051-(Difluoromethyl)-3-nitrobenzene

Product 1

HCID 234451193-(Difluoromethyl)anilineYield 97.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

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

  1. temperaturerefluxed for 15 minutes
  2. custominto room temperature
  3. temperaturerefluxed again for 1 hour
  4. customwere removed
  5. 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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