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

HRID 2269926Notes

Reaction equation

HRID 2269926 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].[Br:13][CH2:14][CH2:15][CH2:16]Br>C(#N)C>[Br:13][CH2:14][CH2:15][CH2:16][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

4

Reactant 2

HCID 80011,3-DibromopropaneHCID 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), K2CO2 (2.9 g, 20.3mmol), 1,3-dibromopropane (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 (2.9 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 (2.9 g)
  9. customwas recrystallized twice from isopropyl ether

Sources & evidence

ORD record
ord-66fecc2ad7524cb5a5d7e679a392e88d
Source dataset
uspto-grants-2001_12
Patent number
USRE037478E1

Reaction notes

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