General Description
1,3,5-Tris(4-bromophenyl)benzene (TBB) is a halogenated aromatic monomer that can be used in the formation of covalent aromatic frameworks(COF).
Synthesis
General method: p-Bromoacetophenone (3 mmol) was mixed with sulfated tungstate (20 wt%) in a round-bottomed flask fitted with a condenser tube and the reaction was carried out with stirring at 130°C. The reaction was monitored by thin film chromatography (TLC). The reaction progress was monitored by thin layer chromatography (TLC). After complete consumption of p-bromoacetophenone, the reaction was continued for 2 hours. After the reaction mixture was cooled, it was diluted with 30 mL of ethyl acetate and filtered to recover the catalyst. The filtrate was sequentially washed with 10 mL of water, dried over anhydrous sodium sulfate and subsequently concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (60-120 mesh) using petroleum ether: ethyl acetate (9:1, v/v) as eluent to give pure 1,3,5-tris(4-bromophenyl)benzene.
References
[1] Synthetic Communications, 2013, vol. 43, # 16, p. 2178 - 2190
[2] RSC Advances, 2015, vol. 5, # 27, p. 21206 - 21214
[3] Journal of the Iranian Chemical Society, 2012, vol. 9, # 5, p. 791 - 798
[4] European Journal of Organic Chemistry, 2014, vol. 2014, # 14, p. 2907 - 2916
[5] Synthetic Communications, 2005, vol. 35, # 24, p. 3167 - 3171
