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

Temperature

80 °C

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 (ca. 80° C.) for 16 h at which point the reaction flask was cooled to room temperature. The resultant solids were filtered off and the solvent removed by rotary evaporation under reduced pressure. The residue was dissolved in Et2O/EtOAc (4:1, 500 mL) and the precipitated solid (the alkylation dimer) 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 crude 1-(5-bromo-2-(2-bromoethoxy)phenyl)ethanone (8.07 g, 55%)

1. temperaturewas cooled to room temperature
2. filtrationThe resultant solids were filtered off
3. customthe solvent removed by rotary evaporation under reduced pressure
4. dissolutionThe residue was dissolved in Et2O/EtOAc (4:1, 500 mL)
5. customthe precipitated solid (the alkylation dimer) 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-e3f13d63a80a43c29ad3472148d9e295

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952043B2