3-Bromobenzaldehyde → 2-Amino-1-(3-bromophenyl)ethan-1-ol

To a cooled solution of 3-bromobenzaldehyde (1.58 mL) in THF (15 mL) were added trimethylsilyl cyanide (1.7 mL) and N,N-diisopropylethylamine (0.23 mL). The mixture was stirred at room temperature for 2d and at reflux for 2 h. The solution was allowed to cool to room temperature and then was slowly added to a cooled suspension of lithium aluminium hydride (769 mg) in THF (10 mL). The mixture was stirred at 0° C. for 10 min, the cooling bath was removed, and the mixture was heated at reflux for 3 h. After cooling to room temperature, ethylacetate was added slowly, followed by a mixture of Na2SO4/silicagel/H2O. After stirring the suspension for 30 min, the mixture was filtered, the filtrate was dried (Na2SO4), and concentrated in vacuo. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH/ammonia 90:10:2) to give (1.59 g) 2-amino-1-(3-bromo-phenyl)-ethanol as a yellow oil.

1. temperatureat reflux for 2 h
2. customthe cooling bath was removed
3. temperaturethe mixture was heated
4. temperatureat reflux for 3 h
5. temperatureAfter cooling to room temperature
6. additionethylacetate was added slowly
7. additionfollowed by a mixture of Na2SO4/silicagel/H2O
8. stirringAfter stirring the suspension for 30 min
9. filtrationthe mixture was filtered
10. dry with materialthe filtrate was dried (Na2SO4)
11. concentrationconcentrated in vacuo
12. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH/ammonia 90:10:2)

ORDレコード

ord-92924f80a4c84f7787d895da1891166a

出典データセット

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08063088B2