반응 #508197

반응 방정식

water

Sodium borohydride

3,5-Dichloro-N-(5-bromo-2-hydroxybenzylidene)aniline

Acetone

→

title compound

수율 93.3%

N-[(5 Bromo-2-hydroxyphenyl)methyl]-3,5-dichloroaniline

수율 93.3%

용매

ethanol

tetrahydrofuran

반응 조건

후처리

1. 1
   기타the residue obtained by concentration under reduced pressure
2. 2
   추출extracted with dichloromethane
3. 3
   세척After the dichloromethane layer was washed with water and brine one after another,
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   기타the solvent was evaporated under reduced pressure
6. 6
   기타The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1)
7. 7
   기타to give a light yellow viscous material
8. 8
   기타This was crystallized by n-hexane

실험 절차

3,5-Dichloro-N-(5-bromo-2-hydroxybenzylidene)aniline (1.04 g, 3 mmol) was dissolved in tetrahydrofuran (12 mL) and ethanol (6 mL). Sodium borohydride (113 mg, 3 mmol) was added under ice cooling and argon atmosphere, and the mixture was stirred at room temperature for 12 hours. Acetone (10 mL) was added to the reaction mixture, and the residue obtained by concentration under reduced pressure was added water and extracted with dichloromethane. After the dichloromethane layer was washed with water and brine one after another, dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1) to give a light yellow viscous material. This was crystallized by n-hexane to give the title compound (971 mg, 93.3%) as a white crystal.

출처