1,3-Dibromopropane → 1-[4-(3-Bromopropoxy)-3,5-dibromophenyl]ethanone

HRID 744210Notes

Reaction equation

HRID 744210 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([Br:10])[C:7]([OH:11])=[C:6]([Br:12])[CH:5]=1)=[O:3].C([O-])([O-])=O.[K+].[K+].[Br:19][CH2:20][CH2:21][CH2:22]Br>C(#N)C>[Br:19][CH2:20][CH2:21][CH2:22][O:11][C:7]1[C:6]([Br:12])=[CH:5][C:4]([C:2](=[O:3])[CH3:1])=[CH:9][C:8]=1[Br:10]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 761581-(3,5-Dibromo-4-hydroxyphenyl)ethan-1-one

Product 1

HCID 219601181-[4-(3-Bromopropoxy)-3,5-dibromophenyl]ethanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 3,5-dibromo-4-hydroxyacetophenone (3.0 g, 10.1 mmol), K2CO3 (2.8 g, 20.3 mmol), 1,3-dibromo- propane (4.0 g, 19.8 mmol) in acetonitrile (100 ml) was heated at reflux for 5 hours. The solvent was removed. The crude product was extracted into dichloromethane (150 ml) and the insoluble inorganics were filtered off. The solution was concentrated to dryness again. Purification was carried out by flash chromatography on silica gel (45 g, SIO2 ; eluted with 1:1 hexane:dichloromethane). The material thus obtained (2.8 g) was recrystallized twice from isopropyl ether to give analytically pure 1-[4-(3-bromopropoxy)-3,5-dibromophenyl]ethanone, m.p.=87°-88° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. customThe solvent was removed
  4. extractionThe crude product was extracted into dichloromethane (150 ml)
  5. filtrationthe insoluble inorganics were filtered off
  6. concentrationThe solution was concentrated to dryness again
  7. customPurification
  8. customThe material thus obtained (2.8 g)
  9. customwas recrystallized twice from isopropyl ether

Sources & evidence

ORD record
ord-c84ca7d185a647f9961f1ee0c51d5dac
Source dataset
uspto-grants-1996_09
Patent number
US05559116

Reaction notes

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