Reaction #2271684

Reaction equation

3,5-dibromo-4-hydroxyacetophenone

K2CO3

1,3-dibromopropane

→

1-[4-(3-bromopropoxy)-3,5-dibromophenyl]ethanone

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperatureat reflux 5 hours
2. 2
   OtherThe solvent was removed
3. 3
   ExtractionThe crude product was extracted into dichloromethane (150 ml)
4. 4
   Filtrationthe insoluble inorganics were filtered off
5. 5
   ConcentrationThe solution was concentrated to dryness again
6. 6
   OtherPurification
7. 7
   OtherThe material thus obtained (2.8 g)
8. 8
   Otherwas recrystallized twice from isopropyl ether

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.

Source