Nitric Acid → 4'-Fluoro-3'-nitroacetophenone

HRID 1636937Notes

Reaction equation

HRID 1636937 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[N+:11]([O-])([OH:13])=[O:12]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 98284'-Fluoroacetophenone

Product 1

HCID 27346124'-Fluoro-3'-nitroacetophenone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-10 °C

Procedure

13.8 g of 4'-fluoroacetophenone (provided from Tokyo Chemical Industry Co., Ltd.) were added in two portions to 100 ml of fuming nitric acid cooled to -10° C. with agitation. After the mixture was warmed to room temperature, the agitation was continued for further 4 hours. This mixture was poured into 1.0 liter of ice water and was extracted with 500 ml of ethyl acetate. The organic layer was dried and the solvent was distilled off under a reduced pressure. The residue was purified by a column chromatography (9/1-4/1: n-hexane/ethyl acetate) twice, whereby 4.16 g of the above-identified were obtained. Rf=0.50 (chloroform).

Workup

  1. temperatureAfter the mixture was warmed to room temperature
  2. extractionwas extracted with 500 ml of ethyl acetate
  3. customThe organic layer was dried
  4. distillationthe solvent was distilled off under a reduced pressure
  5. customThe residue was purified by a column chromatography (9/1-4/1: n-hexane/ethyl acetate) twice
  6. customwhereby 4.16 g of the above-identified were obtained

Sources & evidence

ORD record
ord-e27a8cc3e260498bbde331c4c9187f89
Source dataset
uspto-grants-2000_03
Patent number
US06037362

Reaction notes

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