Sodium Hydroxide → 5-Bromo-2-fluoroaniline

HRID 2200157Notes

Reaction equation

HRID 2200157 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1.[OH-].[Na+]>C(O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH:3]=1)[NH2:9]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 27694075-Bromo-2-fluoroanilineYield 46.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Mix 4-bromo-1-fluoro-2-nitrobenzene (2 g, 9.17 mmol) and stannous chloride dihydrate (8 g, 35 mmol) in ethanol (20 mL), heat the mixture to reflux for 4 hrs. Cool the reaction to room temperature, dilute with water and adjust pH=12 with sodium hydroxide solution, filter off the solid. Partition the filtrate in water and dichloromethane, collect the organic layer, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to give crude product (800 mg, 46.5%). MS: (M+1): 190/192.

Workup

  1. temperatureheat the mixture
  2. temperatureto reflux for 4 hrs
  3. temperatureCool
  4. customthe reaction to room temperature
  5. filtrationfilter off the solid
  6. customPartition the filtrate in water
  7. customdichloromethane, collect the organic layer
  8. dry with materialdry over anhydrous sodium sulfate
  9. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-2c10039d32e34306af4accde637a025f
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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