Water → 3-Bromophenethylamine

HRID 585010Notes

Reaction equation

HRID 585010 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)N.[CH2:9]([N:11](CC)CC)[CH3:10].S(OCC)(OCC)(=O)=O.O>CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:9][NH2:11])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6163Diethyl SulfateHCID 8471TriethylamineHCID 115623-Bromoaniline

Product 1

HCID 70217363-Bromophenethylamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5 g (29.1 mmol) of 3-bromoaniline in 500 ml of ether are introduced into a round-bottomed flask under a stream of nitrogen. 4.5 ml (32 mmol) of triethylamine and 15.2 ml (117 mmol) of diethyl sulfate are added. The medium is refluxed for 24 hours and then left for 8 days at room temperature. It is then poured into water and extracted with ether. The organic phase is washed with saturated aqueous sodium chloride solution and is then dried over magnesium sulfate, filtered and evaporated. The residue is purified by chromatography on a column of silica eluted with a heptane/ethyl acetate mixture (95/5) and 2.5 g (43%) of the expected product are obtained.

Workup

  1. temperatureThe medium is refluxed for 24 hours
  2. extractionextracted with ether
  3. washThe organic phase is washed with saturated aqueous sodium chloride solution
  4. dry with materialis then dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by chromatography on a column of silica
  8. washeluted with a heptane/ethyl acetate mixture (95/5) and 2.5 g (43%) of the expected product
  9. customare obtained

Sources & evidence

ORD record
ord-2eb80dc6f25741ea83fbca062e3fb035
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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