Reaction #157751

Reaction equation

ammonium chloride

Potassium carbonate

3-bromo-1-propanol

4-bromophenol

→

3-(4-bromophenoxy)propan-1-ol

Solvents

water

N,N-dimethylformamide

Conditions

Workup

1. 1
   Temperaturecooling
2. 2
   Temperaturecooled
3. 3
   Extractionfollowed by extraction with a mixture of hexane-ethyl acetate (1:1)
4. 4
   DryingThe organic layer was dried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   OtherThe solvent was then evaporated under reduced pressure
7. 7
   OtherThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1→4:1→3:1)

Procedure

Potassium carbonate (12.0 g) and 3-bromo-1-propanol (5.1 mL) were added to a solution of 4-bromophenol (5.0 g) in N,N-dimethylformamide (200 mL) under ice-cooling, and the mixture was stirred at room temperature for 8.5 hours. The reaction solution was ice-cooled and a saturated ammonium chloride solution and water were added, followed by extraction with a mixture of hexane-ethyl acetate (1:1). The organic layer was dried over sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1→4:1→3:1) to give 3-(4-bromophenoxy)propan-1-ol as a crude product.

Source