Phosphorus tribromide → 1-(Benzyloxy)-4-bromo-2-(bromomethyl)benzene

A mixture of 2-benzyloxy-5-bromobenzaldehyde (14.55 g) and sodium borohydride (2.6 g) in ethanol (250 ml) was stirred under argon for 1 hour. The solvent was evaporated, the residue dissolved in ethyl acetate and added dropwise to 0.1M hydrochloric acid solution (200 ml) at 0° C. The organic solution was washed with saturated aqueous sodium hydrogen carbonate (100 ml) and brine (100 ml), dried (sodium sulphate), filtered and evaporated to give 2-benzyloxy-5-bromobenzyl alcohol (14.85 g) as an oil. To a solution of 2-benzyloxy-5-bromobenzyl alcohol (14.75 g) in diethyl ether (150 ml) was added dropwise, at 0° C., to a solution of phosphorus tribromide (13.68 g) in diethyl ether (40 ml). The mixture was warmed to ambient temperature, diluted with diethyl ether (200 ml) and filtered through a pad of silica gel (200 g) washing with 1 litre of diethyl ether. The combined organic solution was washed with saturated aqueous sodium hydrogen carbonate (150 ml) and brine (150 ml), dried (sodium sulphate), filtered and evaporated to give 2-benzyloxy-5-bromobenzyl bromide (15.2 g).

1. filtrationfiltered through a pad of silica gel (200 g)
2. washwashing with 1 litre of diethyl ether
3. washThe combined organic solution was washed with saturated aqueous sodium hydrogen carbonate (150 ml) and brine (150 ml)
4. dry with materialdried (sodium sulphate)
5. filtrationfiltered
6. customevaporated

ORD record

ord-da4780a542a343368c5cc6703713a64c

Source dataset

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05811459