Sodium Chloride → 4-[4-(Trifluoromethoxy)phenoxy]pyridine

Participants

Reaction Conditions

Reaction Steps

4-Chloropyridine hydrochloride (17.3 g), 4-Trifluoromethoxyphenol (24.6 g), K2CO3 (35.1 g) and DMF (173 mL) were placed in a vessel and stirred at 28-40° C. for 1.5 hr. and then stirred at 75-84° C. for 6 hr. and then stirred at 139-146° C. for 34.5 hr. The reaction mixture was then cooled to room temperature and water (256 mL), a small amount of NaCl and ethyl acetate (256 mL) were added. The organic material was taken up in ethyl acetate. The organic layer was washed with water (256 mL) and a small amount of NaCl. And then the organic layer was extracted three times with 10 v/v % HCl (256 mL×3). The organic material was taken up in 10 v/v % HCl. And then the aqueous layer was basified to pH 9 by NaOH and was extracted with ethyl acetate (256 mL). The organic material was taken up in ethyl acetate. The organic layer was washed with water (256 mL) and a small amount of NaCl. The organic layer was condensed under reduced pressure to give 15.3 g (52.0% yield) of a brown oily target compound.

Provenance & Evidence