Dinitrofluorobenzene → 2-Fluoro-5-nitroaniline
Reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[F:13])([O-])=O>[Fe]>[F:13][C:5]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[NH2:1]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
European Patent Application 127,079, Takemoto et al. (1984), discloses a process in which 2,4-dinitrofluorobenzene is selectively reduced using between 2.5 and 4 moles of iron in the presence of acid to produce one mole of 2-fluoro-5-nitroaniline. In one example in which acetic acid was employed and the reaction mixture was refluxed for ten minutes, 2-fluoro-5-nitroaniline was produced in 70% yield, by weight. The weight % ratio of the desired 2-fluoro-5-nitroaniline to the by-product 4-fluoro-3-nitroaniline was 93:7. The use of a noble metal catalyst is not taught by this patent application.
Sources & evidence
- ORD record
- ord-4061488e7da54391806aed2ceca7532e
- Source dataset
- uspto-grants-1992_04
- Patent number
- US05105012
Reaction notes
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