Potassium Nitrate → 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-])([O-:12])=[O:11].[K+]>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
- 28 °C
Procedure
To a stirred solution of 1-bromo-2,4-difluorobenzene (0.512 g, 2.65 mmol, Aldrich, used as received) in conc. H2SO4 (5.0 mL) at 0° C., KNO3 (0.275 g, 2.72 mmol) was added in one lot. The resulting solution was allowed to warm to 28° C. and stirred at that temperature overnight. It was then poured into ice (50 g) and extracted with ethyl acetate (50 mL). The ethyl acetate was dried over anhydrous Na2SO4, removed under vacuum and the resulting oil dried further under vacuum to afford 0.576 g (91%) of the pure (1H NMR) title compound as a light red oil; 1H NMR (CDCl3); δ 7.141 (dd, 1H, J1 =10.2 Hz, J2 =7.8 Hz), 8.375 (t, 1H, J=7.5 Hz).
Workup
- extractionextracted with ethyl acetate (50 mL)
- dry with materialThe ethyl acetate was dried over anhydrous Na2SO4
- customremoved under vacuum
- customthe resulting oil dried further under vacuum
Sources & evidence
- ORD record
- ord-fa24f556f97140cfaae6f8d364879954
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06147075
Reaction notes
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