1-Bromo-2-fluoro-3-nitrobenzene → 3-Bromo-2-fluoroaniline

HRID 1811052Notes

Reaction equation

HRID 1811052 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[F:11]>C(O)C.C(O)(=O)C.O.[Fe]>[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:5]=[CH:6][CH:7]=1)[NH2:8]

Participants

4

Reactant 1

HCID 404274461-Bromo-2-fluoro-3-nitrobenzene

Product 1

HCID 223418913-Bromo-2-fluoroanilineYield 93%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 86584229Acetic acid ethanol waterSolvent

Procedure

A solution of 1-bromo-2-fluoro-3-nitrobenzene (1.10 g, 5.00 mmol) in ethanol-acetic acid-water (2:2:1) (25 mL) was treated with iron powder (1.396 g, 25.0 mmol) and the mixture was heated at reflux for 1 h. The mixture was cooled to rt and filtered through a Celite pad. The filtrate was concentrated and the residue was partitioned between EtOAc and NaHCO3 (aq). The organic phase was washed with brine, dried and concentrated to provide 3-bromo-2-fluoroaniline as a brown oil (880 mg, 93%). 1H NMR (400 MHz, chloroform-d) δ 6.85-6.92 (1H, m), 6.80 (1H, td, J=8.0, 1.2 Hz), 6.66-6.73 (1H, m), 3.81 (2H, br. s.).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 h
  3. filtrationfiltered through a Celite pad
  4. concentrationThe filtrate was concentrated
  5. customthe residue was partitioned between EtOAc and NaHCO3 (aq)
  6. washThe organic phase was washed with brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ccb6405c5cc54b75af38d057cf98e713
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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