反应详情

A mixture of 5-bromo-2-chloro-4-hyroxybenzonitrile (compound 87, 38.1 g, 164 mmol), dimethyl sulfate (20.1 mL, 213 mmol), and lithium hydroxide monohydrate (8.93 g, 213 mmol) in THF (500 mL) was refluxed overnight. The mixture was cooled to ambient temperature and then diluted with EtOAc. The EtOAc solution was washed with water and brine prior to drying over anhydrous MgSO4. Filtration and removal of the voletiles under reduced pressure left the crude product which was purified by column chromatography (5-40% EtOAC/hexanes) to yield 5-bromo-2-chloro-4-methoxybenzonitrile (30.7 g, 76%) as a white solid.

1. temperaturewas refluxed overnight
2. washThe EtOAc solution was washed with water and brine
3. dry with materialto drying over anhydrous MgSO4
4. filtrationFiltration and removal of the voletiles under reduced pressure
5. waitleft the crude product which
6. customwas purified by column chromatography (5-40% EtOAC/hexanes)