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

HRID 1459937Notes

Reaction equation

HRID 1459937 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-a0a6ca452c8746c2b90384757fc8d688
Source dataset
uspto-grants-1998_12
Patent number
US05854263

Reaction notes

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