(R)-2-(1-amino-2-(2,5-dibromophenyl)ethyl)-5-bromopheno synthesis
- Product Name:(R)-2-(1-amino-2-(2,5-dibromophenyl)ethyl)-5-bromopheno
- CAS Number:1585969-24-9
- Molecular formula:C14H12Br3NO
- Molecular Weight:449.96
![Phenol, 5-bromo-2-[2-(2,5-dibromophenyl)-1-iminoethyl]-](/CAS/20180703/GIF/1585969-22-7.gif)
1585969-22-7
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Yield: 93%
Reaction Conditions:
with sodium tetrahydroborate;methyl bisulfate;(R)-α,α-diphenylprolinol in 1,2-dimethoxyethane at -20 - 0; for 16 h;Reagent/catalyst;Solvent;
Steps:
(R)-2-[1-Amino-2-(2,5-dibromophenyl)ethyl]-5- bromophenol
A mixture of sodium borohydride (18.87 g, 496.57 mmol, 0.37 eq) with 1,2-DME (3 L, 5 v) was cooled down to -20°C, stirred for 15 min, and MSA (154.63 g, 1610.72 mmol, 1.2 eq) was added followed by R-diphenylprolinol (170.0 g, 691.73 mmol, 0.5 eq). (Z)-2- [1-Amino-2-(2,5-dibromophenyl)vinyl]-5-bromophenol (10) (600.28 g, 1343.85 mmol, 1.0 eq) was added at -20°C, and the mixture was stirred for 12 h. Upon completion of the process (TLC), the reaction mixture was poured into 25% ammonium chloride solution (2 L) at 0°C and extracted with ethyl acetate (3 L). To the organic layer saturated aqueous sodium bicarbonate was added and pH was adjusted to 7.0. The organic layer was separated and washed with 25% sodium chloride solution (2 L), concentrated and dissolved in acetonitrile (3 L), followed by slow addition of water (3 L) over 1 h. The solid product was fi ltered off under the atmosphere of nitrogen and dried to give the product (3) as white crystals (559 g, 93%, 99 ee).
References:
Chapala, Vijaya Lakshmi;Katari, Naresh Kumar;Kerru, Nagaraju;Malavattu, Giri Prasad;Marisetti, Vishnu Murthy;Reddy, Pedavenkatagari Narayana [Russian Journal of General Chemistry,2021,vol. 91,# 5,p. 932 - 938]
203314-28-7
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