2,6-Lutidine → (E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile

Participants

Reaction Steps

[step 6] (E)-2-[3-fluoro-8-(hydroxymethyl)dibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (13.3 g, 45.0 mmol) obtained in step 5 was dissolved in THF (450 mL), methanesulfonic anhydride (19.6 g, 112.6 mmol), lithium bromide (23.5 g, 270.2 mmol) and 2,6-lutidine (31.5 mL, 270.2 mmol) were added, and the mixture was stirred at room temperature for 13 hr. To the mixture was added water (200 mL), and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were washed with 1 mol/L hydrochloric acid (100 mL), saturated aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0 v/v-97/3 v/v) to give the title compound (13.4 g, 83%).

Provenance & Evidence