Water → 4-Bromo-5-fluoro-2-methoxyaniline

HRID 2283512Notes

Reaction equation

HRID 2283512 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-])=O)=[CH:4][C:3]=1[F:13].[Cl-].[NH4+].O>C(O)(C)C.[Fe]>[Br:1][C:2]1[C:3]([F:13])=[CH:4][C:5]([NH2:10])=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 223473121-Bromo-2-fluoro-5-methoxy-4-nitrobenzene

Product 1

HCID 223472984-Bromo-5-fluoro-2-methoxyanilineYield 93.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 1-bromo-2-fluoro-5-methoxy-4-nitrobenzene (0.998 g, 3.99 mmol) in isopropanol (20 mL) was added iron (0.7 g, 12 mmol), ammonium chloride (0.64 g, 12 mmol) and water (2 mL). The reaction was stirred at 75° C. for 2 hours, then filtered and concentrated. The residue was diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to give 4-bromo-5-fluoro-2-methoxyaniline (0.82 g, 93%).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additionThe residue was diluted with water
  4. extractionextracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f2e0f3a2495b45b3ad9d1063fd992323
Source dataset
uspto-grants-2015_09
Patent number
US09145402B2

Reaction notes

Loading…