Uses
4-Dihydrochromone is a class of natural compounds with excellent biological activities, including anticancer, antibacterial, anti-inflammatory, and anti-allergic activities, as well as antiplatelet aggregation activities. 6-Bromo-4-dihydrochromone is a derivative of 4-dihydrochromone and can be used as a pharmaceutical intermediate.
Synthesis
3-(4-Bromophenoxy)propionic acid (150 g, 0.61 mol) was slowly added to 1.0 liter of concentrated sulfuric acid at room temperature with continuous stirring for 1 hour. Upon completion of the reaction, the mixture was carefully poured into 500 g of ice water, whereupon a white solid precipitated. The white solid was separated by filtration and dried naturally in air. The crude product was purified by recrystallization using ethanol, resulting in 89 g (64% yield) of the target compound 6-bromobenzodihydropyran-4-one as a white solid.
References
[1] E-Journal of Chemistry, 2012, vol. 9, # 3, p. 1251 - 1256
[2] Patent: CN106699716, 2017, A. Location in patent: Paragraph 0022; 0035
[3] Australian Journal of Chemistry, 2010, vol. 63, # 11, p. 1582 - 1593
[4] Journal of the American Chemical Society, 1951, vol. 73, p. 4205,4207
[5] Tetrahedron, 2017, vol. 73, # 27-28, p. 3913 - 3922
