9-(3,5-Diphenylphenyl)bromoanthracene synthesis

Yield:478495-51-1 74%

Reaction Conditions:

with sodium carbonate;tetrakis(triphenylphosphine) palladium⁽⁰⁾ in water;toluene; for 10 h;Heating / reflux;

Steps:

2.2

Under an atmosphere of argon, 9-(3,5-dibromophenyl)anthracene (5 g, 12 mmole), phenylboric acid (4.4 g, 36 mmole, 3 eq) and tetrakis(triphenylphosphine)palladium(0) (0.55 g, 0.48 mmole, 2% Pd) were dissolved in toluene (100 ml). To the obtained solution, a 2M aqueous solution of sodium carbonate (11 g, 0.10 moles, 3 eq/50 ml) was added, and the resultant mixture was refluxed for 10 hours. The obtained reaction mixture was filtered, and an organic layer was separated from the filtrate, washed with a saturated aqueous solution of sodium chloride (50 ml) and dried with magnesium sulfate. After the solvent was removed by distillation, a black oily substance was obtained. The obtained oily substance was purified in accordance with the column chromatography (silica gel/hexane, hexane + 3% dichloromethane, hexane + 10% dichloromethane in the final step), and a light yellow amorphous solid substance (3.6 g, 74%) was obtained. The obtained product was identified to be 9-(3,5-diphenyl- phenyl)anthracene in accordance with1H-NMR and FDMS. 1H-NMR (CDCl3, TMS) δ: 7.3-7.6 (10H, m), (1H, s), 7.7-7.9 (8H, m), 8.01 (1H, s), 8.05 (2H, dd, J=9 Hz, 2 Hz), 8.52 (1H, s). FDMS: calcd. for C32H22=406, found m/z=406 (M+, 100)

References:

EP1496041,2005,A1 Location in patent:Page 23