Sodium Iodide → 1-Bromo-4-phenylmethoxybenzene

To a solution of 4-bromophenol (20.0 g, 116 mmol) dissolved in DMF (100 ml) were added successively benzyl bromide (13.7 ml, 116 mmol), potassium carbonate (47.9 g, 347 mmol) and sodium iodide (1.7 g, 11.6 mmol), and the mixture was stirred for 4 hr at room temperature. Insoluble material was filtered off and water (500 ml) was added to the obtained filtrate. The precipitate was collected by filtration and the obtained precipitate was dissolved in diethyl ether (300 ml). The mixture was washed with water (100 ml) and saturated brine (100 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated. The obtained residue was washed with cold hexane and dried to give the title compound (26.2 g, 86%) as a white solid.

1. filtrationInsoluble material was filtered off
2. additionwater (500 ml) was added to the obtained filtrate
3. filtrationThe precipitate was collected by filtration
4. dissolutionthe obtained precipitate was dissolved in diethyl ether (300 ml)
5. washThe mixture was washed with water (100 ml) and saturated brine (100 ml)
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. concentrationconcentrated
8. washThe obtained residue was washed with cold hexane
9. customdried

ORD record

ord-bd4859e812c148d69ecb634b52b75905

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610729B1