ENNVIROMENTALLY BENIGN SYNTHESIS OF BROMINATED FLAVONE

• Main Author: YERICO HAMONANGAN SIMANGUNSONG (NIM:10514008), JOSUA
• Format: Final Project
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/28333
• Institution: Institut Teknologi Bandung

Flavones are phenolic compounds found in terrestrial plants in nature. Flavone compounds and their <br /> <br /> <br /> <br /> derivatives have been known to have various biological activities such as antioxidants, antiinflammatory, <br /> <br /> <br /> <br /> antibacterial, anticancer, and antimicrobial. So that, they have a lot of potensial to be developed in the <br /> <br /> <br /> <br /> health and food industry. In this study, synthesis of flavone compounds was carried out using the MAOS <br /> <br /> <br /> <br /> method by using imidazolium ionic liquid. Imidazolium ionic liquid ([BMIM]Cl) was synthesized from <br /> <br /> <br /> <br /> 1-chlorobutane and 1-methylimidazole with a 1: 1 ratio reacted by using CEM microwaves with 300 <br /> <br /> <br /> <br /> watts of power, 75 oC for 80 minutes. [BMIM]Cl ionic liquid synthesis produced a mass of 22.21 grams <br /> <br /> <br /> <br /> with a yield of 88.84%. Then the synthesis of flavone compounds was carried out. Flavone compound <br /> <br /> <br /> <br /> synthesized from 1-(1,2-hydroxyphenyl)-3-phenyl-1,3-propandion compound and ionic fluid [BMIM]Cl <br /> <br /> <br /> <br /> was inserted into the vial then reacted using CEM microwave with 150 watts of power, 150 0C for 10 <br /> <br /> <br /> <br /> minute. The synthesis of this compound produces a mass of 32.30 mg with a yield of 37.30%. After that, <br /> <br /> <br /> <br /> bromination was done to flavone so that it can be a precursor for the synthesis of substituted flavone <br /> <br /> <br /> <br /> compounds, which has bioactivity like sinensetin, vitexin, etc. As a model reaction, oxidative bromination <br /> <br /> <br /> <br /> was done to anisol using HBr and H2O2 with methanol and glacial acetic acid as the solvent at <br /> <br /> <br /> <br /> temperature of 40-50 oC. Bromination of anisol produced a mass of 1.55 gram with a yield of 44.70%. <br /> <br /> <br /> <br /> Bromination of flavone using the same method resulted in a product with a mass of 60 mg with a yield of <br /> <br /> <br /> <br /> 45.80%. The structure of each product in this research had been confirmed by 1H NMR analysis