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

HRID 1955870Notes

Reaction equation

HRID 1955870 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-f3ecea61baf940d8a30c06ab05d1411d
Source dataset
uspto-grants-1998_07
Patent number
US05776963

Reaction notes

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