2-Fluoroaniline → 4-Bromo-2-fluoroaniline

HRID 648288Notes

Reaction equation

HRID 648288 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[Br:9]C1C(=O)C(Br)=CC(Br)(Br)C=1.[OH-].[Na+]>C(Cl)Cl>[Br:9][C:7]1[CH:6]=[CH:5][C:3]([NH2:4])=[C:2]([F:1])[CH:8]=1

Participants

5

Reactant 3

HCID 95842-FluoroanilineHCID 14798Sodium HydroxideHCID 884332,4,4,6-Tetrabromocyclohexa-2,5-dienone

Product 1

HCID 1230504-Bromo-2-fluoroaniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of o-fluoroaniline (3.9 g) in methylene chloride (50 ml), cooled to -20° under nitrogen, is added a solution of 2,4,4,6-tetrabromocyclohexadienone (35 mmol) in methylene chloride. After several hours, reaction is poured into 15% NaOH solution. The layers are separated and the organic fraction shaken against 15% NaOH solution. The methylene chloride fraction is washed with saturated NaCl solution, dried over calcium sulfate and evaporated to yield 4-bromo-2-fluoroaniline.

Workup

  1. waitAfter several hours
  2. customreaction
  3. customThe layers are separated
  4. washThe methylene chloride fraction is washed with saturated NaCl solution
  5. dry with materialdried over calcium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-9198f28879124f1db409a776ca9b86ab
Source dataset
uspto-grants-1983_10
Patent number
US04411912

Reaction notes

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