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

HRID 2184502Notes

Reaction equation

HRID 2184502 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-dibromopropane (4.0 g, 19.8 mmol) in acetonitrile (100 ml) was heated at reflux 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. temperatureat reflux 5 hours
  2. customThe solvent was removed
  3. extractionThe crude product was extracted into dichloromethane (150 ml)
  4. filtrationthe insoluble inorganics were filtered off
  5. concentrationThe solution was concentrated to dryness again
  6. customPurification
  7. customThe material thus obtained (2.8 g)
  8. customwas recrystallized twice from isopropyl ether

Sources & evidence

ORD record
ord-d171568b8b3e45cc93a374d7c135dd3d
Source dataset
uspto-grants-2002_06
Patent number
USRE037729E1

Reaction notes

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