C1COCCN1.COCCOc1cc(I)cc([N+](=O)[O-])c1>CC(=O)O.CC(=O)O.Cc1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>COCCOc1cc(N2CCOCC2)cc([N+](=O)[O-])c1
diacetoxypalladium (0.087 g, 0.39 mmol) was added to a stirred mixture of 1-iodo-3-(2-methoxyethoxy)-5-nitrobenzene (2.5 g, 7.74 mmol), cesium carbonate (7.56 g, 23.21 mmol) and morpholine (0.880 mL, 10.06 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.482 g, 0.77 mmol) dissolved in toluene (80 mL) and dioxane (20 mL) over a period of 10 minutes, degased and under argon. The resulting suspension was heated at 110 °C for 15 hours.Solvents were evaporated and the mixture was adsorbed with ammonia/methanol 7N on silica gel.The crude product was purified by flash chromatography on silica gel eluting with 40 to 60% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford 4-(3-(2-methoxyethoxy)-5-nitrophenyl)morpholine (2.000 g, 92 %) as a orange solid.
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