Reaction #64426

Reaction equation

1-bromopentane

3-Bromophenol

potassium carbonate

→

3-bromo-phenol

n-pentyl ether

Solvents

dimethylformamide

Conditions

Workup

1. 1
   Temperaturecooled to room temperature
2. 2
   Filtrationfiltered
3. 3
   workup.ADDITIONThe filtrate is diluted with ether
4. 4
   Washwashed with water and brine
5. 5
   DryingAfter drying over magnesium sulfate
6. 6
   Concentrationconcentrating
7. 7
   Otherthe crude oil obtained
8. 8
   Otheris chromatographed over silica gel
9. 9
   Washeluted with 3:2 hexane

Procedure

To a solution of 5.0 gm of 3-Bromophenol in 60 mls of dimethylformamide is added 6.0 gm of potassium carbonate followed by 4.3 ml of 1-bromopentane. This mixture is heated to 60° C. for 6 hours and then cooled to room temperature and filtered. The filtrate is diluted with ether and washed with water and brine. After drying over magnesium sulfate and concentrating, the crude oil obtained is chromatographed over silica gel, and eluted with 3:2 hexane:ether to yield 3-bromo-phenol, n-pentyl ether as a clear oil.

Source