4-Hydroxybenzaldehyde → 4-(2-Bromoethoxy)Benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-hydroxybenzaldehyde (10.0 g, 82 mmol) and potassium carbonate (46 g, 326 mmol) was placed into 2 L round bottom flask, and DMF (150 mL) was added. The mixture was stirred for 45 min. and dibromoethane (46 g) was added in one portion, then the reaction mixture was allowed to stir at 25-35° C. for 96 hrs under a nitrogen atmosphere. The reaction mixture was cooled to 25-35° C. and then poured into water (500 mL). The mixture was extracted with EtOAc (3×100 mL), combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography over silicagel by using 10-15% ethyl acetate/pet. ether to afford the title compound (8.50 g, 45%) as a white solid.

Provenance & Evidence