Hydrochloric Acid → 1-(4-Bromo-2-chlorophenyl)ethan-1-one

To a stirred solution of methylmagnesium iodide (0.82 M solution in diethylether; 113 ml, 92.4 mmol) was added a solution of 4-bromo-2-chlorobenzonitrile (10 g, 46.2 mmol) in diethylether (92 ml) dropwise, and the mixture was heated at reflux temperature for 16 hours. The mixture was cooled down to room temperature, added concentrated hydrochloric acid (50 ml), and the mixture was stirred for 5 hours. The whole was extracted with diethylether. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:10) to give title compound (7.77 g, 72% yield).

1. temperaturethe mixture was heated
2. temperatureat reflux temperature for 16 hours
3. extractionThe whole was extracted with diethylether
4. washThe organic layer was washed with brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo
7. customThe residue was purified by flash chromatography
8. washeluting with ethyl acetate-hexane (1:10)

ORD record

ord-19aaa69fb31b4777a16476c163e4df5e

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06727238B2