Iodoethane → 4-Bromo-5-ethoxy-2-fluoroaniline

HRID 566185Notes

Reaction equation

HRID 566185 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](I)[CH3:12].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:9][C:5]1[C:6]([O:8][CH2:11][CH3:12])=[CH:7][C:2]([NH2:1])=[C:3]([F:10])[CH:4]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 109656515-Amino-2-bromo-4-fluorophenol

Product 1

HCID 132814294-Bromo-5-ethoxy-2-fluoroanilineYield 67.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Amino-2-bromo-4-fluorophenol (10.30 g), ethyl iodide (9.36 g) and potassium carbonate (7.59 g) were suspended in acetonitrile (100 ml), and the mixture was heated under refluxing for about 6 hours. After the reaction, the precipitates were filtered, the solvent was distilled off, extracted with ethyl acetate, and 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 v/v) to obtain the objective 4-bromo-5-ethoxy-2-fluoroaniline (7.93 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder refluxing for about 6 hours
  3. customAfter the reaction
  4. filtrationthe precipitates were filtered
  5. distillationthe solvent was distilled off
  6. extractionextracted with ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThen, ethyl acetate was distilled off
  9. customthe resulting oily substance was purified by chromatography on silica gel (ethyl acetate:n-hexane=1:3 v/v)

Sources & evidence

ORD record
ord-a7297898309f4a7787c521b4ba54118e
Source dataset
uspto-grants-2001_01
Patent number
US06174839B1

Reaction notes

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