1,3-Dibromopropane → N-[3-(3-Bromo-propoxy)-phenyl]-acetamide

HRID 2394694Notes

Reaction equation

HRID 2394694 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:18][CH2:19][CH2:20][CH2:21]Br>ClCCl>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[O:11][CH2:21][CH2:20][CH2:19][Br:18])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 121243-Hydroxyacetanilide

Product 1

HCID 6420330N-[3-(3-Bromo-propoxy)-phenyl]-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-acetamidophenol (15.1 g) in dichloromethane (500 ml, dry) was added potassium carbonate (20 g) and then 1,3-dibromopropane (30 g). The resulting mixture was heated at reflux for 6 hours and then overnight at room temperature. After an additional 24 hours, the reaction was complete. Solids were filtered from the reaction mixture, and the solution was concentrated to an oil, which was purified to yield 3-(3-acetamidophenoxy)propyl bromide, 13.2 g.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 6 hours
  3. customovernight
  4. customat room temperature
  5. filtrationSolids were filtered from the reaction mixture
  6. concentrationthe solution was concentrated to an oil, which
  7. customwas purified

Sources & evidence

ORD record
ord-cb4d9de627b448b884314f5d69427706
Source dataset
uspto-grants-1998_09
Patent number
US05811435

Reaction notes

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