Benzyl Bromide → 1-(Benzyloxy)-3-bromobenzene

Temperature

80 °C

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.

1. additionTo this was added portionwise
2. additionUpon completion of addition
3. temperatureto cool to ambient temperature
4. extractionThe mixture was extracted with 600 mL of diethyl ether
5. washThe extract was then washed with three 50 mL portions of water
6. concentrationit was concentrated under reduced pressure to a residual solid
7. customThe solid was recrystallized with 250 mL of methanol

ORD record

ord-da5e29d180a54664a82e18d39541a7df

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05627189