Potassium Carbonate → Isovanillin

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3-[5-(4-Amino-benzyl)-2-methoxy-phenoxy]-benzonitrile P-15. In an 8 mL vial equipped with a stir bar was placed (18) (250 mg, 0.798 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (192 mg, 0.878 mmol), potassium carbonate (331 mg, 2.39 mmol), 1,5-bis(diphenylphosphino)pentane (105 mg, 0.239 mmol), and dimethylformamide (4.5 mL). The mixture was degassed with nitrogen for 15 minutes and allylpalladium(II) chloride dimer (43.8 mg, 0.120 mmol) was added. The mixture was heated to 85° C. for 18 hours. The reaction mixture was filtered through celite and to the filtrate were added water (30 mL) and saturated ammonium chloride solution (30 mL). After extractions with ethyl acetate (2×75 mL), the organic portions were combined, washed with brine (50 mL), dried (MgSO4) and concentrated. The crude material was purified by silica gel column chromatography utilizing 50% ethyl acetate/hexanes to produce 118 mg (45% yield) of P-15 as a yellow viscous oil. MS (APCI+): 331.1 (M+1), LC-MS: >99%

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