Materials Uses
3-Fluoro-4-bromobenzyl bromide (4BFBB) is an organic compound that is a member of the class of halogenated aromatic compounds. This molecule has a set of isomers, which are in the same family and have the same chemical formula but different arrangements of atoms. 4BFBB has been used as an acceptor material for organic solar cells with experimental success. It absorbs light in the visible spectrum and transfers electrons to pbdb-t, increasing the efficiency of solar cells. The fluorine atoms in 4BFBB interact with other molecules due to their high electronegativity, making them useful for chemical reactions.
Synthesis
General procedure for the synthesis of 3-fluoro-4-bromobenzyl bromide from 3-fluoro-4-bromotoluene: To a reaction flask was added a solution of 4-bromo-3-fluorotoluene (21.5 g, 0.114 mol) in acetonitrile (200 ml), followed by N-bromosuccinimide (NBS; 21.2 g, 0.119 mol). The mixture was heated to reflux and dibenzoyl peroxide (1.4 g, 0.004 mol) was added as initiator and the reaction was kept at reflux for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and extracted with water. The aqueous phase was separated and discarded, the organic phase was washed with saturated brine and dried over anhydrous sodium sulfate. Finally, the solvent was removed by vacuum concentration to afford the target product 3-fluoro-4-bromobenzyl bromide as an oil (27.1 g, 90% yield).
References
[1] Patent: WO2011/15287, 2011, A2. Location in patent: Page/Page column 13
[2] Patent: US2011/39934, 2011, A1. Location in patent: Page/Page column 5
[3] Patent: EP2700643, 2014, A1. Location in patent: Paragraph 0234
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 7, p. 2293 - 2306
[5] Journal of Medicinal Chemistry, 2005, vol. 48, # 18, p. 5705 - 5720
