N,N-Dimethylglycine → 3-(5-Formyl-2-methoxy-phenoxy)-benzonitrile

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In a 350 mL pressure vessel equipped with a stir bar was placed 3-hydroxy-4-methoxy-benzaldehyde (15) (1.5 g, 9.86 mmol), 3-iodo-benzonitrile (3.39 g, 14.8 mmol), cesium carbonate (3.21 g, 9.86 mmol), N,N-dimethylglycine (275 mg, 1.97 mmol), copper(I) iodide (188 mg, 0.986 mmol) and 1,4-dioxane (55 mL). The mixture was heated to 100° C. for 46 hours. The reaction was cooled to room temperature, quenched with water (300 mL) and then extracted with ethyl acetate (3×200 mL). The organic portions were combined, washed with brine (300 mL), dried (MgSO4) and concentrated. The crude material was purified by silica gel column chromatography utilizing 35%, 50%, 75% ethyl acetate/hexanes to produce 1.09 g (42% yield) of (16) as a white solid.

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