Synthesis
GENERAL METHODS: Trifluoroacetic acid (0.045 mL, 0.6 mmol) and ethylenediamine (0.020 mL, 0.3 mmol) were sequentially added to an anhydrous nitromethane (1.5 mL) solution of 3'-bromoacetophenone (1.5 mmol). The reaction mixture was stirred under reflux conditions and the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was cooled to room temperature and the reaction was quenched with saturated ammonium chloride (NH4Cl) solution followed by extraction with ethyl acetate. The organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. Finally, the crude product was purified by silica gel column chromatography to give 1,3,5-tris(3-bromophenyl)benzene.
References
[1] Tetrahedron Letters, 2012, vol. 53, # 19, p. 2436 - 2439
[2] Comptes Rendus Chimie, 2013, vol. 16, # 3, p. 252 - 256
[3] Journal of Chemical Research, 2007, # 12, p. 720 - 721
[4] Synthetic Communications, 2012, vol. 42, # 24, p. 3579 - 3588
[5] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p. 1251 - 1258
