p-Bromoacetophenone → 1-(4-(2-(Diethylamino)ethoxy)phenyl)ethanone

Participants

Reaction Steps

A mixture of 4-bromoacetophenone (5 g, 25 mmol), the diethylaminoethanol (3.5 g, 38 mmol), K2CO3 (2g), copper powder (0.5 g) and copper(I) iodide (2.5 g) in DMSO (30 ml) was heated at 120° C. until TLC showed consumption of the starting material. After cooling to RT, the mixture was poured onto aqueous NH3 (28%, 100 ml), extracted with CH2Cl2 (3×100 ml). The combined organic extracts were dried (Na2SO4), filtered and the CH2Cl2 distilled in vacuo. The crude product was purified by column chromatography on silica gel, eluting with EtOAc-MeOH (95:5) to furnish the pure compound (4.85 g, 82%).

Provenance & Evidence