Hydrochloric Acid → 3-Bromo-5-fluoro-2-methylaniline

HRID 2353105Notes

Reaction equation

HRID 2353105 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[CH3:12].Cl>CO.C(Cl)Cl.[Fe]>[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([NH2:9])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 27733851-Bromo-5-fluoro-2-methyl-3-nitrobenzene

Product 1

HCID 27376413-Bromo-5-fluoro-2-methylanilineYield 28.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of crude 1-bromo-5-fluoro-2-methyl-3-nitro-benzene (5.96 g) in MeOH (90 mL) was added concentrated hydrochloric acid (11.7 mL) and iron (6.1 g) and the reaction mixture was heated to reflux. After 16 h, the mixture was cooled, diluted with DCM, washed with sodium carbonate solution, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using flash chromatography to yield 3-bromo-5-fluoro-2-methyl-phenylamine (1.46 g).

Workup

  1. temperaturethe reaction mixture was heated to reflux
  2. temperaturethe mixture was cooled
  3. washwashed with sodium carbonate solution
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-5d46f5552a4a40f1baf94a52cce28024
Source dataset
uspto-grants-2010_07
Patent number
US07750002B2

Reaction notes

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