1,3,5-Tris(4-bromophenyl)benzene

White to tan solid

General procedure: In round bottom flask equipped with condenser a mixture of aryl alkyl ketones (3mmol) and sulfated tungstate (20 wt. percent) were stirred at 130 C, the progress of the reaction was monitored by TLC. After disapperance of the aryl alkyl ketones and the reaction was continued for additional time of 2 h. The reaction mixture was cooled, diluted with 30 mL of ethyl acetate and filtered to recover the catalyst. The filtrate was washed with 10 mL of water, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel ( 60-120) with (PE:EA=9:1) as eluent to get pure 1, 3, 5-arylenzenes.General procedure: A mixture of acetophenone (3 mmol) and DBSA (0.6 mmol) was heated at 130 °C in a preheated oil bath for 3–8 hours. After completion of the reaction as indicated by thin layer chromatography (TLC), the reaction mixture was cooled to room temperature and diluted with equal volumes of saturated solution of NaHCOGeneral procedure: To a solution of aryl methyl ketone (1, 1.5mmol) in dry nitromethane (1.5mL) was added trifluoroacetic acid (0.045 mL, 0.6mmol) and ethylenediamine (0.020 mL, 0.3mmol). The mixture was stirred at reflux and detected by TLC. After completion of the reaction, the reaction mixture was cooled to room temperature, quenched with saturated NH4Cl, extracted with Ethyl acetate. Combined organic layers were washed with brine, dried over Na2SO4, and concentrated. The residue was purified by silica gel column chromatography to give product 2.4-Bromoacetophenone (7.962 g, 40 mmol) and ethyl orthoformate ester (8 mL, 48 mmol) were dissolved in benzene (24 mL) in a flask. Gaseous hydrogen chloride was bubbled through the solution at room temperature and under stirring for 3 h. The solution became brownish-red colored and the precipitate formation began during the first hour. The resulting precipitate was filtered off, washed with acetone and methanol, and dried. The yield of product recrystallized from chloroform was 43.6percent. The 1H NMR spectrum of synthesized product (see Fig. 1) was completely corresponded to that of 1, 3, 5-tris(4-bromophenyl)benzene. 1H NMR (500 MHz), δ: 7.68 (s, 3 H); 7.60 (d, 6 H, J = 8.5 Hz); 7.53 (d, 6 H, J = 8.5 Hz).In a 100 mL-flask, 2.45 g of the last product of compound 13, 60 mL of a 47percent aqueous HBr solution, and 0.5 g of tetrabutylammonium bromide were added, and the mixture was heated under reflux with nitrogen for 6 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate, washed twice with water, and the solvent was evaporated under reduced pressure to obtain 2.11 g of a crude product of Compound 14. The crude product was dissolved in 60 mL of DMF, 4.22 g of PPh3PBr2 was added, and the reaction was refluxed with nitrogen for 12 hours. After cooling to room temperature, the solvent is distilled off and the residue is dissolvedAfter ethyl acetate was washed with water twice, the solvent was distilled off again and silica gel column chromatography gave 2.77 g of compound 15 in a yield of 85percent.

Molecular Weight:543.1
XLogP3:9.7
Rotatable Bond Count:3
Exact Mass:541.87034
Monoisotopic Mass:539.87239
Heavy Atom Count:27
Complexity:364
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes