Nitric Acid → 1-Bromo-2,4-difluoro-5-nitrobenzene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[F:9].[N+:10]([O-])([OH:12])=[O:11]>OS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]([F:8])=[CH:4][C:3]=1[F:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of 1-bromo-2,4-difluorobenzene (6.0 mL, 53.0 mmol) in concd H2SO4 (38.5 mL) at 0° C. was added dropwise concd HNO3 (34.0 mL) maintaining an internal temperature below 20° C. The resulting mixture was stirred for 30 min at 0° C., then poured slowly into ice water with vigorous stirring. The aqueous phase was separated and extracted with EtOAc. The combined organic extracts were washed with 5% aqueous KOH and brine, dried over MgSO4 and concentrated to give 12.2 g (51.5 mmol, 97%) of 1-bromo-2,4-difluoro-5-nitrobenzene: 1H NMR (400 MHz, CDCl3) δ 8.39 (t, 1 H, J=7.4 Hz), 7.13 (dd, 1 H, J=7.7, 10.3 Hz).
Workup
- temperaturemaintaining an internal temperature below 20° C
- customThe aqueous phase was separated
- extractionextracted with EtOAc
- washThe combined organic extracts were washed with 5% aqueous KOH and brine
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-aeb546b784894e7b9d39dc6e9eff9cd3
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199135B2
Reaction notes
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