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

HRID 30821Notes

Reaction equation

HRID 30821 reaction equation
O.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:11])[CH3:10].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[F:2][C:3]1[CH:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[CH:5][C:4]=1[C:9](=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 96744o-Fluoroacetophenone

Product 1

HCID 27810671-(2-Fluoro-5-nitrophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent3×

Procedure

In a 3-neck flask equipped with an internal thermometer was added sulfuric acid and cooled to −10° C. in an ice/salt/water batch. 2′-fluoroacetophenone(1 eq) in sulfuric acid was added dropwise over 10 minutes via addition funnel to produce a solution of 0.2M. Nitric acid (1.15 eq) in sulfuric acid was then added dropwise at a rate not to exceed 5° C. After complete addition resulting solution was allowed to stir at for 30 minutes. Solution was poured onto ice and extracted with ethyl acetate. Organics were washed with a saturated solution of sodium bicarbonate, brine, dried with sodium sulfate and concentrated. Crude product was purified using flash chromatography (85% Hex:15% EtoAc) on silica to afford 1-(2-fluoro-5-nitrophenyl)ethanone.

Workup

  1. customIn a 3-neck flask equipped with an internal thermometer
  2. customto produce a solution of 0.2M
  3. customto exceed 5° C
  4. additionAfter complete addition
  5. customresulting solution
  6. additionSolution was poured onto ice
  7. extractionextracted with ethyl acetate
  8. washOrganics were washed with a saturated solution of sodium bicarbonate, brine
  9. dry with materialdried with sodium sulfate
  10. concentrationconcentrated
  11. customCrude product was purified

Sources & evidence

ORD record
ord-6bccb15750864f96b01b595ff9affa02
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Reaction notes

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