Allyl bromide → 5-Allyloxy-4-bromo-2-fluoroaniline

HRID 566195Notes

Reaction equation

HRID 566195 reaction equation
[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Br:9])=[C:6]([OH:8])[CH:7]=1.[CH2:11](Br)[CH:12]=[CH2:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:13]([O:8][C:6]1[C:5]([Br:9])=[CH:4][C:3]([F:10])=[C:2]([CH:7]=1)[NH2:1])[CH:12]=[CH2:11]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 109656515-Amino-2-bromo-4-fluorophenol

Product 1

HCID 212655985-Allyloxy-4-bromo-2-fluoroanilineYield 32.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Amino-2-bromo-4-fluorophenol (30.9 g), allyl bromide (21.8 g) and potassium carbonate (22.77 g) were suspended in acetonitrile (300 ml), and the mixture was stirred at room temperature for 12 hours. After the reaction, the precipitates were filtered, the solvent was distilled off, and this was extracted with ethyl acetate. After washing with water, it was dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off and the resulting oily substance was purified by chromatography on silica gel (ethyl acetate:n-hexane=1:3) to obtain the objective 5-allyloxy-4-bromo-2-fluoroaniline (12.14 g).

Workup

  1. customAfter the reaction
  2. filtrationthe precipitates were filtered
  3. distillationthe solvent was distilled off
  4. extractionthis was extracted with ethyl acetate
  5. washAfter washing with water, it
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. distillationThen, ethyl acetate was distilled off
  8. customthe resulting oily substance was purified by chromatography on silica gel (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-b3d8c62272b443e0bc028e62b5887f53
Source dataset
uspto-grants-2001_01
Patent number
US06174839B1

Reaction notes

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