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

HRID 2307430Notes

Reaction equation

HRID 2307430 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]>OS(O)(=O)=O>[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 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 4′-fluoroacetophenone (111.04 g) in concentrated H2SO4 (46 mL) was dropwise added a thoroughly mixed solution of fuming nitric acid (6.4 mL) and concentrated H2SO4 (118 mL) at 15° C. After the addition was complete, the reaction mixture was stiffed at −15° C. for 30 min and then poured into ice-water. The resulting mixture was extracted with CH2Cl2, and the organic layer was washed with water, dried over MgSO4 and concentrated in vacuo. The resulting residue was Purified by silica gel flash chromatography (30% ethyl acetate in hexane) to give 5.6 g of the title compound as a solid.

Workup

  1. additionAfter the addition
  2. extractionThe resulting mixture was extracted with CH2Cl2
  3. washthe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was Purified by silica gel flash chromatography (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8508b56b2c26418788a5d273435997c2
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

Loading…