4'-Bromoacetanilide → 4-bromo-N-ethylaniline

To a suspension of lithium aluminum hydride (1.1 g, 29 mmol) in anhydrous tetrahydrofuran (70 ml) was added dropwise at 0° C. a solution of N-(4-bromophenyl)acetamide (2.5 g, 12 mmol) in anhydrous tetrahydrofuran (30 ml). The reaction mixture was warmed to room temperature, and stirred for 15 mins. After further stirring at 60° C. for 2 hrs, the mixture was cooled to 0° C. Water (1.8 ml) was added dropwise by small portions, and 2M aqueous sodium hydroxide solution (1.55 ml) was added dropwise. After stirring for 15 mins, sodium sulfate was added, and the mixture was further stirred for 15 mins. The mixture was filtered through a Celite pad, and the insoluble material was washed with dichloromethane. The filtrate and washing solution were combined and concentrated under reduced pressure to give 4-bromo-N-ethylaniline (2.28 g, yield 95%) as a yellow oil.

1. stirringAfter further stirring at 60° C. for 2 hrs
2. temperaturethe mixture was cooled to 0° C
3. additionwas added dropwise
4. stirringAfter stirring for 15 mins
5. stirringthe mixture was further stirred for 15 mins
6. filtrationThe mixture was filtered through a Celite pad
7. washthe insoluble material was washed with dichloromethane
8. washThe filtrate and washing solution
9. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-32d094858c69455c9e79d060f77bebd9

Quelldatensatz

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08999989B2