Nitric Acid → 1-(2-Fluoro-5-nitrophenyl)propan-1-one

HRID 1941782Notes

Reaction equation

HRID 1941782 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:11])[CH2:9][CH3:10].[N+:12]([O-])([OH:14])=[O:13].O>S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]=1[C:8](=[O:11])[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 5793991-(2-Fluorophenyl)propan-1-one

Product 1

HCID 179677821-(2-Fluoro-5-nitrophenyl)propan-1-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of the 1-(2-fluoro-phenyl)-propan-1-one (99 mmol) in concentrated sulfuric acid (80 ml) cooled down to −30° C. was added slowly fuming nitric acid (8 ml) over 20 min and the solution was stirred at −30° C. for 15 min. The mixture was slowly poured into a stirred mixture of 200 ml of water and 400 g of ice. The aqueous phase was extracted with ethyl acetate, the organic layer was extracted again with water and aqueous 1 M NaHCO3-solution. The organic layer was dried over Na2SO4, evaporated and the residue was chromatographed on silica using a mixture of heptane and ethylacetate as eluent to afford 16.5 g of the pure nitro intermediate XII-1. MS (ESI): m/z=198.1 [M+H]+.

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. extractionthe organic layer was extracted again with water and aqueous 1 M NaHCO3-solution
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated
  5. customthe residue was chromatographed on silica using
  6. additiona mixture of heptane and ethylacetate as eluent

Sources & evidence

ORD record
ord-32a4e7583d804d978d6e837a52c4aff9
Source dataset
uspto-grants-2013_03
Patent number
US08389513B2

Reaction notes

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