4-Phenoxyphenol → 2,2-Dimethyl-5-nitro-5-(6-(4-phenoxyphenoxy)naphthalen-2-yl)-1,3-dioxane

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Reaction Conditions

Reaction Steps

5-(6-Bromo-naphthalen-2-yl)-2,2-dimethyl-5-nitro-1,3-dioxinane (0.2719 g, 0.0007425 mol) (Example 10), 4-phenoxyphenol (0.2074 g, 0.001114 mol), copper(I) iodide (0.0141 g, 0.0000742 mol) cesium carbonate (0.4838 g, 0.001485 mol) and N,N-dimethylglycine HCl (0.0311 g, 0.000223 mol) were placed in a 40 mL reaction vial equipped with a magnetic stir bar. The vial was capped and flushed with nitrogen. The gas was then removed under vacuum. The flask was again flushed with nitrogen, evacuated and filled with nitrogen. 1,4-Dioxane (4 mL, 0.05 mol) was then added via syringe and the mixture was flushed with nitrogen and evacuated several times. The mixture was then heated to 90° C. and stirred overnight. TLC analysis showed that the reaction was complete. The cooled mixture was partitioned between EtOAc and water. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to dryness under reduced pressure. The residual oil was loaded on a silica gel column and eluted with ethylacetate:hexane (20:80) to afford 286 mg of the title compound (82% yield).

Provenance & Evidence