Ethanol → 2-Bromoanisole

Into a three-necked flask of 1liter, 25g (0.145 mol) of o-bromophenol, 6.1 g (0,152mol) of sodium hydroxide and 300 ml of ethanol were charged and refluxed for two hours. Then, 82.0 g (0.578 mol) of methyl iodide was added dropwise and the mixture was refluxed further for four hours. After the mixture was cooled to room temperature, 600 ml of diethyl ether was added. The mixture was charged into a separatory funnel. Separated organic layer was washed successively with, 100 ml of 2N-hydrochloric acid cooled with ice, 300 ml of saturated sodium thiosulfate, and water until the washings were neutral. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The concentrate was distilled under reduced pressure to obtain 25.3 g (0.135 mol) of o-methoxyphenylbromide.

1. temperaturerefluxed for two hours
2. temperaturethe mixture was refluxed further for four hours
3. additionThe mixture was charged into a separatory funnel
4. washSeparated organic layer was washed successively with, 100 ml of 2N-hydrochloric acid
5. temperaturecooled with ice, 300 ml of saturated sodium thiosulfate, and water until the washings
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. customthe solvent was removed by distillation under reduced pressure
8. distillationThe concentrate was distilled under reduced pressure

ORD record

ord-15af841dab684444b99547c16e152820

Source dataset

uspto-grants-1995_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05395766