Reaction equation
[N+]([O-])(O)=O.OS(O)(=O)=O.F[C:11]1C=CC=C(C)C=1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21](C)[C:20]=1[N+:29]([O-:31])=[O:30]>>[F:18][C:19]1[CH:24]=[C:23]([CH3:11])[C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=1[N+:29]([O-:31])=[O:30]Participants
5
Procedure
To a stirred solution of HNO3 (60 mL) and H2SO4 (80 mL), cooled in an ice bath, was added 1-fluoro-3-methyl-benzene (27.5 g, 25 mmol) at such a rate that the temperature did not rise over 35° C. The mixture was allowed to stir for 30 min at room temperature and poured into ice water (500 mL). The resulting precipitate (a mixture of the desired product and 1-fluoro-3-methyl-2,4-dinitro-benzene, approx. 7:3) was collected via filtration and purified by recrystallization from 50 mL isopropyl ether to give 1-fluoro-5-methyl-2,4-dinitro-benzene as a white solid (18 g, 36%).
Workup
- customdid not rise over 35° C
Sources & evidence
- ORD record
- ord-864084c6a15d43038ce1102be4fcd1e0
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829204B2
Linked notes
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