4-Bromo-2-fluoro-6-nitrotoluene → 5-Bromo-3-fluoro-2-methylaniline

HRID 1962380Notes

Reaction equation

HRID 1962380 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:10]([O-])=O)[C:5]([CH3:9])=[C:6]([F:8])[CH:7]=1>C(O)C.O.Cl.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH3:9])=[C:4]([NH2:10])[CH:3]=1

Participants

6

Reactant 1

HCID 27733874-Bromo-2-fluoro-6-nitrotoluene

Product 1

HCID 27376405-Bromo-3-fluoro-2-methylaniline

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 5-bromo-1-fluoro-2-methyl-3-nitro-benzene (9.96 g) and iron powder (11.9 g) in ethanol (100 ml), water (20 ml) and concentrated hydrochloric acid (2 ml) was heated at reflux for one hour. After cooling, the reaction mixture was filtered through hyflo (calcined diatomaceous earth) and concentrated. The residue was purified by chromatography on silica gel (ethyl acetate/cyclohexane 1:9 to 1:4). Yield: 7.06 g of 5-bromo-3-fluoro-2-methyl-phenylamine as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for one hour
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered through hyflo (calcined diatomaceous earth)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (ethyl acetate/cyclohexane 1:9 to 1:4)

Sources & evidence

ORD record
ord-50f6017d80134150bcf27a55a4bf97b5
Source dataset
uspto-grants-2013_04
Patent number
US08415369B2

Reaction notes

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