Ammonium Chloride → 2-(8-bromo-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile

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[step 3] Commercially available diethyl 1-cyanoethylphosphonate (38.0 g, 199 mmol) was dissolved in THF (170 mL), LDA (99.0 mL, 199 mmol, 2.0 mol/L heptane/THF/ethylbenzene solution) was added dropwise at 0° C., and the mixture was stirred at 0° C. for 1 hr. 8-Bromo-3-fluorodibenzo[b,e]oxepin-11(6H)-one (30.5 g, 99.0 mmol) obtained in step 2 and dissolved in THF (120 ml) was added to the reaction system, and the mixture was stirred at room temperature for 1 hr. To the mixture was added saturated aqueous ammonium chloride solution (500 mL), and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-80/20 v/v) to give 2-(8-bromo-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (31.4 g, 92%, E/Z=1/1).

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