반응 #74506

반응 방정식

5-bromo-2-chloro-4-hyroxybenzonitrile

compound 87

5-bromo-2-chloro-4-hyroxybenzonitrile

dimethyl sulfate

lithium hydroxide monohydrate

→

5-bromo-2-chloro-4-methoxybenzonitrile

수율 76.0%

용매

EtOAc

THF

반응 조건

후처리

1. 1
   온도was refluxed overnight
2. 2
   세척The EtOAc solution was washed with water and brine
3. 3
   건조to drying over anhydrous MgSO4
4. 4
   여과Filtration and removal of the voletiles under reduced pressure
5. 5
   workup.WAITleft the crude product which
6. 6
   기타was purified by column chromatography (5-40% EtOAC/hexanes)

실험 절차

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.

출처