Dimethylformamide → 2-((4-Bromobenzyl)oxy)pyridine

Participants

Reaction Conditions

Reaction Steps

To a N,N-dimethylformamide solution (125 mL) of 4-bromobenzyl alcohol (25 g, 130 mmol) was added potassium tert-butoxide (15.8 g, 141 mmol) at room temperature, which was stirred for 10 minutes at 54° C. To this reaction solution was added 2-fluoropyridine (15 mL, 154 mmol) at a temperature ranging from 40° C. to 58° C., which was stirred for another 30 minutes at 65° C. The reaction solution was cooled to room temperature, water and ethyl acetate were added thereto, which was separated. The aqueous layer was further extracted with ethyl acetate twice. The ethyl acetate layers were combined, washed with water three times and saline once, and was then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure. Diethyl ether was added to the residue, and this was concentrated under a reduced pressure, so as to obtain a crude product of the title compound (34 g).

Provenance & Evidence