4'-Hydroxyacetophenone → 2-Bromo-1-(4-hydroxyphenyl)ethanone

Participants

Reaction Steps

4-Hydroxyacetophenone (25 g) was treated with bromine (9.5 mL) dropwise over 15 minutes in THF (60 mL) at room temperature and stirred until the color was consumed. The whole was carefully poured into saturated sodium bicarbonate solution until basic. The aqueous layer was extracted with ether (3×100 mL) and the ether layer was washed with saturated sodium bicarbonate solution (100 mL) followed by 5% aqueous sodium bisulfite (100 mL), H2O (100 mL) and finally saturated brine solution (100 mL). The organic layer was dried over MgSO4, filtered and concentrated to provide an oil (30 g) of crude material used in the preparation of thiazoles.

Provenance & Evidence