Water → 3-Bromo-6-fluoro-2-methylbenzenamine
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([N+:9]([O-])=O)[C:3]=1[CH3:12].[NH4+].[Cl-].O>CCO.[Fe]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([NH2:9])[C:3]=1[CH3:12]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 1-bromo-4-fluoro-2-methyl-3-nitro-benzene (3 g, 12.82 mmol, 1.0 eq) in EtOH (60 mL) was added NH4Cl (30 mL), water (30 mL) and iron powder (2.87 g, 51.28 mmol, 4.0 eq). The reaction mixture was heated at reflux for 3h, then filtered through Celite. The filtrate was evaporated in vacuo and purified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:10) to give the title compound as a yellow solid (2 g, 77%).
Workup
- temperatureThe reaction mixture was heated
- filtrationfiltered through Celite
- customThe filtrate was evaporated in vacuo
- custompurified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:10)
Sources & evidence
- ORD record
- ord-aeb1ebc553bf47c198af5002db95fe6c
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249085B2
Reaction notes
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