Nitric Acid → 1-(2-Fluoro-5-nitrophenyl)ethan-1-one
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].OS(O)(=O)=O.[N+:16]([O-])([OH:18])=[O:17]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:16]([O-:18])=[O:17])=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9]Participants
4
Conditions
- Temperature
- -15 °C
Procedure
2′-Fluoroacetophenone (11.04 g) was dropwise added to concentrated H2SO4 (46 mL) at −20° C. After the addition was complete, a thoroughly mixed solution of fuming nitric acid (6.4 mL) and concentrated H2SO4 (18 mL) was added dropwise at −15° C. The reaction mixture was stirred at −15° C. for 15 minutes and then poured into 500 g of ice. The resulting solid was collected, washed with and dissolved in CH2Cl2. The organic layer was washed with water, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel flash chromatography (25% ethyl acetate in hexane) to give 8 g of the title compound as a solid.
Workup
- additionAfter the addition
- customThe resulting solid was collected
- washwashed with and
- dissolutiondissolved in CH2Cl2
- washThe organic layer was washed with water
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel flash chromatography (25% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-4d74e68da8e9480c8b85aa0323cfb1ab
- Source dataset
- uspto-grants-2004_12
- Patent number
- US06831080B2
Reaction notes
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