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
The diacetoxypalladium (0.337 g, 1.50 mmol) was added to a stirred mixture of 1-iodo-3-(2-methoxyethoxy)-5-nitrobenzene (9.7 g, 30.02 mmol), cesium carbonate (29.3 g, 90.07 mmol) and morpholine (3.41 mL, 39.03 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (1.869 g, 3.00 mmol) dissolved in toluene (200 mL) and dioxane (50 mL) The reaction was degased, purged with argon and heated at 110 °C for 15 hours. The mixture was diluted with dichloromethane (250ml) the salts were fitered, the filtrate was concentrated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 15% ethyl acetate in dichloromethane. The solvent was evaporated to dryness to afford 4-(3-(2-methoxyethoxy)-5-nitrophenyl)morpholine (4.50 g, 53.1 %) as a orange solid.
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