Acetone → 1-(3-Bromopropoxy)-4-chlorobenzene

HRID 1729288Notes

Reaction equation

HRID 1729288 reaction equation
C(=O)([O-])[O-].[K+].[K+].CC(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.[Br:19][CH2:20][CH2:21][CH2:22]Br>C(C(C)=O)C>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:22][CH2:21][CH2:20][Br:19])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 46844-ChlorophenolHCID 80011,3-DibromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 2235341-(3-Bromopropoxy)-4-chlorobenzeneYield 75.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

10 g of potassium carbonate was added to 30 ml of a methyl ketone solution containing 15.9 g of p-chlorophenol, and the solution was then heated with stirring at 60° C. for 1 hour. Afterward, 30 ml of a methyl ethyl ketone solution containing 50 g of 1,3-dibromopropane was added dropwise; After the addition, the solution was heated under reflux for 3 hours. The reaction solution was then cooled and a precipitate was removed therefrom, and the solution was evaporated to dryness under reduced pressure to obtain 23.2 g of 4-chlorophenoxypropyl bromide.

Workup

  1. temperaturethe solution was then heated
  2. additionwas added dropwise
  3. additionAfter the addition
  4. temperaturethe solution was heated
  5. temperatureunder reflux for 3 hours
  6. temperatureThe reaction solution was then cooled
  7. customa precipitate was removed
  8. customthe solution was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a6dcaf1910614b82a9bb381eb9670e4c
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

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