1,2-Dibromoethane → 1-[5-Bromo-2-(2-bromoethoxy)phenyl]ethanone

Participants

Reaction Steps

To a stirred solution of 1-(5-bromo-2-hydroxyphenyl)ethanone (9.66 g, 44.9 mmol) in 2-butanone (100 mL) was added potassium carbonate (13 g, 94 mmol) then 1,2-dibromoethane (19.4 mL, 225 mmol). The reaction mixture was heated to reflux and stirred for 16 h. The crude mixture was filtered was washed with acetone, and the filtrate was concentrated in vacuo. The residue was treated with a mixture of diethyl ether/EtOAc (4:1; 250 mL) and the resulting solid was removed by filtration. The filtrate was washed with 2 M NaOH (150 mL), dried over sodium sulfate and concentrated in vacuo to give 1-(5-bromo-2-(2-bromoethoxy)phenyl)ethanone (9.0 g, 28.0 mmol, 62% yield) as a light yellow solid. 1H NMR (500 MHz, chloroform-d) δ 7.96-7.80 (m, 1H), 7.63-7.48 (m, 1H), 6.82 (d, J=8.7 Hz, 1H), 4.41 (t, J=5.7 Hz, 2H), 3.73 (t, J=5.7 Hz, 2H), 2.77-2.63 (m, 3H).

Provenance & Evidence