Nitric Acid → 1-(2-Fluoro-5-nitrophenyl)ethan-1-one
Reaction equation
OS(O)(=O)=O.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13](=[O:15])[CH3:14].[N+:16]([O-])([OH:18])=[O:17]>O>[F:6][C:7]1[CH:12]=[CH:11][C:10]([N+:16]([O-:18])=[O:17])=[CH:9][C:8]=1[C:13](=[O:15])[CH3:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
A 2-L round-bottomed flask equipped with a mechanic stirrer was charged with concentrated H2SO4 (360 mL) and cooled to −40° C. 1-(2-Fluorophenyl)ethanone 1 (90.0 g, 652 mmol) was then added followed by addition of a mixture of fuming HNO3 (53.1 mL) and concentrated H2SO4 (129 mL) dropwise over 35 min. The resulting solution was stirred at −40° C. for 30 min and then slowly poured into ice (1.3 kg). The resulting mixture was diluted with water (1 L) and filtered. The filter cake was dissolved in EtOAc (1 L) and the filtrate was extracted with EtOAc (1 L). The combined organics were washed with 5% aqueous sodium carbonate (2×300 mL), water (300 mL), and brine (300 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford 2 (115 g, 97%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 8.79 (dd, J=6.2, 2.9 Hz, 1H), 8.41 (dt, J=8.9, 3.4 Hz, 1H), 7.34 (t, J=9.3 Hz, 1H), 2.71 (d, J=4.8 Hz, 3H).
Workup
- customA 2-L round-bottomed flask equipped with a mechanic stirrer
- filtrationfiltered
- dissolutionThe filter cake was dissolved in EtOAc (1 L)
- extractionthe filtrate was extracted with EtOAc (1 L)
- washThe combined organics were washed with 5% aqueous sodium carbonate (2×300 mL), water (300 mL), and brine (300 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-0045ceb20df849629a3777b0743eac77
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08557826B2
Reaction notes
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