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

To a stirred solution of 5′-bromo-2′-hydroxyacetophenone (10 g, 46.5 mmol) in methyl ethyl ketone (100 mL) was added K2CO3 (13.5 g, 97.7 mmol) followed by 1,2-dibromoethane (20 mL, 232.5 mmol). The reaction mixture was heated at a mild reflux temperature for 16 h then cooled to room temperature. The reaction mixture was filtered and then concentrated in vacuo. The resultant residue was dissolved in diethyl ether/ethyl acetate (4:1, 500 mL) and the precipitated solid was removed by filtration. The filtrate was washed with 2 N NaOH (100 mL) and the organic portion was dried over Na2SO4 and concentrated in vacuo to give 1-[5-bromo-2-(2-bromo-ethoxy)-phenyl]-ethanone (8.07 g, 55%) which was used in the subsequent step without further purification.

1. temperatureThe reaction mixture was heated at a mild reflux temperature for 16 h
2. filtrationThe reaction mixture was filtered
3. concentrationconcentrated in vacuo
4. dissolutionThe resultant residue was dissolved in diethyl ether/ethyl acetate (4:1, 500 mL)
5. customthe precipitated solid was removed by filtration
6. washThe filtrate was washed with 2 N NaOH (100 mL)
7. dry with materialthe organic portion was dried over Na2SO4
8. concentrationconcentrated in vacuo

ORD record

ord-3dabcdea5ca04f2c86639c36949a81db

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08343955B2