Uses
(R)-(+)-1-(4-Bromophenyl)ethylamine is used as a reactant to synthesize a chiral photochromic Schiff base compound by reacting with the salicylaldehyde of an azobenzene derivative, and reacts with brown precipitates at 298 K under a nitrogen atmosphere to yield an orange compound[4].
Synthesis
General procedure for the synthesis of 1-(4-bromophenyl)ethylamine from 1-(4-bromophenyl)ethylamine: 600 g of R-mandelic acid is added to a mixture of 2900 ml of isopropanol and 1500 ml of ethanol and heated to 60°C to dissolve completely. Subsequently 790 g of 4-bromophenethylamine is slowly added (note the exothermic reaction). After the reaction solution cooled naturally to room temperature, it was allowed to stand overnight with continuous stirring during the period. The solid product was collected by filtration and dried to give 660 g of crystals. The resulting crystals were dissolved in a mixture of 2000 ml of isopropanol and 1100 ml of ethanol, heated to 60°C to dissolve the crystals completely, and then cooled to room temperature. After standing overnight, the reaction mixture was stirred, the solid product was collected by filtration and washed with a small amount of acetone and dried to give 510 g of crystals. It was neutralized to basicity with 4M sodium hydroxide solution and subsequently extracted three times with dichloromethane. The organic phases were combined, dried and concentrated to give a final 260.7 g of colorless liquid product in 33% yield.
References
[1] Patent: CN106957255, 2017, A. Location in patent: Paragraph 0059-0061; 0073-0075; 0087-0089
[2] Chemical Communications, 2013, vol. 49, # 77, p. 8629 - 8631
[3] ChemCatChem, 2014, vol. 6, # 4, p. 992 - 995
[4]
Moriwaki, R., Akitsu, T. (2015). Crystal structure of 2-{(
R)-[1-(4-bromophenyl)ethyl]iminomethyl}-4-(phenyldiazenyl)phenol, a chiral photochromic Schiff base. Acta Crystallographica Section E Crystallographic Communications, 71(11), o886–o887.
https://doi.org/10.1107/s2056989015019866
