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

Participants

Reaction Conditions

Reaction Steps

To a N,N-dimethylformamide (125 mL) solution of 4-bromobenzyl alcohol (25 g, 130 mmol) was added potassium tert-butoxide (15.8 g, 141 mmol) at room temperature, which was stirred at 54° C. for 10 minutes. To the reaction solution was added 2-fluoropyridine (15 mL, 154 mmol) was added at a temperature from 40° C. to 58° C., which was stirred at 65° C. for 30 minutes. The reaction solution was cooled to room temperature, and partitioned into water and ethyl acetate. The water layer was further extracted with ethyl acetate (twice). The ethyl acetate layers were combined, washed with water (3 times) and aqueous sodium chloride (once), dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under a reduced pressure. To the residue was added diethyl ether, which was then concentrated under a reduced pressure to obtain the title compound (34 g) as a crude product.

Provenance & Evidence