Reaktion #528156

Reaktionsgleichung

3-bromophenol

potassium carbonate

phenylmethyl bromide

→

3-(phenylmethoxy)phenyl bromide

Ausbeute 89.5%

Lösungsmittel

N,N-dimethylformamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONTo this was added portionwise
2. 2
   workup.ADDITIONUpon completion of addition
3. 3
   Temperaturto cool to ambient temperature
4. 4
   ExtraktionThe mixture was extracted with 600 mL of diethyl ether
5. 5
   WaschenThe extract was then washed with three 50 mL portions of water
6. 6
   Einengenit was concentrated under reduced pressure to a residual solid
7. 7
   SonstigeThe solid was recrystallized with 250 mL of methanol

Vorschrift

Under a nitrogen atmosphere, a solution of 50.0 grams (0.29 mole) of 3-bromophenol and 120.0 grams (0.87 mole) of potassium carbonate in 400 mL of N,N-dimethylformamide was stirred, and heated to 80° C. To this was added portionwise, 36.1 mL (0.30 mole) of phenylmethyl bromide during a 20 minute period. Upon completion of addition, the reaction mixture was stirred at 80° C. during a one hour period. After this time, the reaction mixture was allowed to cool to ambient temperature, where it was diluted with 600 mL of water. The mixture was extracted with 600 mL of diethyl ether. The extract was then washed with three 50 mL portions of water, and then it was concentrated under reduced pressure to a residual solid. The solid was recrystallized with 250 mL of methanol, yielding 68.3 grams of 3-(phenylmethoxy)phenyl bromide. The NMR spectrum was consistent with the proposed structure.

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