Nitric Acid → N-(3-Fluoro-4-nitrophenyl)acetamide
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[NH:5][C:6](=[O:8])[CH3:7].S(=O)(=O)(O)O.[N+:17]([O-])([OH:19])=[O:18].C(Cl)Cl>O>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:17]([O-:19])=[O:18])[NH:5][C:6](=[O:8])[CH3:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 7.5 °C
Procedure
Added 3′-fluoroacetanilide (3.06 g, 20 mmol) cautiously to conc sulfuric acid (6 mL) at 5° C. To the resulting solution, added fuming nitric acid (1.05 mL, 25 mmol) dropwise while maintaining temperature at 5-10° C. After 30 min, added ice (50 g), later diluted with water (100 mL) and extracted with EtOAc (2×100 mL). The combined organic layers were washed with saturated NaHCO3 and brine, dried (Na2SO4) and concentrated to give the crude product (4.0 g) as a mixture of isomers (1:1.4 ratio of 4′-nitro/2′-nitro). The desired isomer, 3′-flouro-4′-nitroacetanilide, was isolated by flash chromatography (DCM-5% MeOH/DCM) in low yield (1.2 g, 30%) as a yellow solid. 1H-NMR (CDCl3): δ 8.08 (1H, app t), 7.82 (1H, dd), 7.41 (1H, br s), 7.21 (1H, m), 2.25 (3H, s).
Workup
- extractionextracted with EtOAc (2×100 mL)
- washThe combined organic layers were washed with saturated NaHCO3 and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customto give the crude product (4.0 g)
- additionas a mixture of isomers (1:1.4 ratio of 4′-nitro/2′-nitro)
Sources & evidence
- ORD record
- ord-f4cf5c5911d24217b0366192558de8d6
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06696473B2
Reaction notes
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