Water → 3-Bromo-6-fluoro-2-methylbenzenamine

HRID 1771651Notes

Reaction equation

HRID 1771651 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

HCID 962WaterHCID 25517Ammonium ChlorideHCID 585404001-Bromo-4-fluoro-2-methyl-3-nitrobenzene

Product 1

HCID 585401563-Bromo-6-fluoro-2-methylbenzenamineYield 77%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

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

  1. temperatureThe reaction mixture was heated
  2. filtrationfiltered through Celite
  3. customThe filtrate was evaporated in vacuo
  4. 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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