C1COCCN1.Oc1ccc(Br)cc1>CC(C)(C)[O-].CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd]>Oc1ccc(N2CCOCC2)cc14-Bromophenol (865 mg, 5 mmol), Tris(dibenzylideneacetone)dipalladium(0) (229 mg, 0.25 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (238 mg, 0.50 mmol), Morpholine (0.437 mL, 5.00 mmol) and sodium tert-butoxide (1009 mg, 10.50 mmol) were stirred in toluene (5 mL) overnight at 100 °C. The mixture was allowed to cool to ambient temperature. Ethylacetate was added and the mixture was washed with aqueous NaHCO3 (satd.) and water. The organic phase was separated, dried over MgSO4, filtered and the solvent removed by rotary evaporation. The crude product was added to a silica gel column and was eluted with 0-2 % MeOH in DCM. The collected fraction were combined and the solvent was removed by rotary evaporation. 1H NMR in CDCl3 is consistent with desired product MS (m+1) = 180. HPLC Peak RT = 2.55 minutes is product. Purity = 96%.
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