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

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).

1. temperatureThe reaction mixture was heated
2. temperatureto reflux
3. filtrationThe crude mixture was filtered
4. washwas washed with acetone
5. concentrationthe filtrate was concentrated in vacuo
6. additionThe residue was treated with a mixture of diethyl ether/EtOAc (4:1; 250 mL)
7. customthe resulting solid was removed by filtration
8. washThe filtrate was washed with 2 M NaOH (150 mL)
9. dry with materialdried over sodium sulfate
10. concentrationconcentrated in vacuo

ORD record

ord-68b058434410479991fecd06d9c8bbe9

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604024B2