反応 #74506

反応方程式

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

収率 76.0%

溶媒

EtOAc

THF

反応条件

後処理

1. 1
   温度was refluxed overnight
2. 2
   洗浄The EtOAc solution was washed with water and brine
3. 3
   乾燥to drying over anhydrous MgSO4
4. 4
   ろ過Filtration and removal of the voletiles under reduced pressure
5. 5
   workup.WAITleft the crude product which
6. 6
   その他was purified by column chromatography (5-40% EtOAC/hexanes)

実験手順

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.

出典