1-Bromo-3-chloropropane → 1-[3-(3-Chloropropoxy)phenyl]ethanone

HRID 1072021Notes

Reaction equation

HRID 1072021 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.Br[CH2:12][CH2:13][CH2:14][Cl:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:15][CH2:14][CH2:13][CH2:12][O:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 84873-HydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 143487521-[3-(3-Chloropropoxy)phenyl]ethanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3′-hydroxyacetophenone (5 g) and 1-bromo-3-chloropropane (5.0 mL) in acetone (40 mL) was treated with potassium carbonate (8.1 g). The mixture was stirred at reflux temperature for 17 hours. The reaction was cooled to ambient temperature and filtered. The filtrate was concentrated in vacuo. The residue was partitioned between dichloromethane (50 mL) and H2O (50 mL). The aqueous phase was washed with two fresh portions of dichloromethane. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered and evaporated to yield the title compound (8.6 g) which was used without further purification.

Workup

  1. temperatureat reflux temperature for 17 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was partitioned between dichloromethane (50 mL) and H2O (50 mL)
  5. washThe aqueous phase was washed with two fresh portions of dichloromethane
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-2d924346a0a544ad901e85d64e9cafa9
Source dataset
uspto-grants-2005_06
Patent number
US06908929B2

Reaction notes

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