1-Bromo-4-fluoro-5-methyl-2-nitrobenzene → 2-Bromo-5-fluoro-4-methylaniline
Reaction equation
[Br:1][C:2]1[C:3]([N+:10]([O-])=O)=[CH:4][C:5]([F:9])=[C:6]([CH3:8])[CH:7]=1>C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([F:9])=[CH:4][C:3]=1[NH2:10]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
Iron powder (18.5 g) was added to a solution of 5-bromo-2-fluoro-4-nitrotoluene (9.7 g) in acetic acid (30 ml), and the mixture was stirred at 70° C. for 3 hours. The catalyst was removed by filtration through Celite, and the filtrate was washed with chloroform. The solvent and the like in the filtrate were distilled off under reduced pressure. The residue was subjected to column chromatography on silica gel to conduct elution with chloroform, thereby obtaining the title compound (7.9 g) as a red oil.
Workup
- customThe catalyst was removed by filtration through Celite
- washthe filtrate was washed with chloroform
- distillationThe solvent and the like in the filtrate were distilled off under reduced pressure
- washelution with chloroform
Sources & evidence
- ORD record
- ord-b35a5741b64740b282bda99be200b36e
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06136823
Reaction notes
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