Hydrochloric Acid → 2-Fluoro-6-octyloxypyridine-3-boronic acid

Participants

Reaction Steps

34.62 ml (69.24 mmol) of a 2-molar solution of lithium diisopropylamide in tetrahydrofuran/hexane/ethylbenzene are added dropwise at -78° C. to 13.00 g (57.70 mmol) of 2-fluoro-6-octyloxypyridine in 200 ml of tetrahydrofuran, and the mixture is stirred for 4 hours. 26.05 g (138.48 mmol) of triisopropyl borate are then added dropwise at -78° C., and the reaction mixture is stirred overnight, during which it warms to room temperature. After addition of 80 ml of 10% hydrochloric acid and stirring at room temperature for 1 hour, sodium chloride solution is added, the mixture is extracted with ether, the ether phase is washed with sodium chloride solution, dried over sodium sulfate, filtered and concentrated. Recrystallization from acetonitrile gives 9.03 g (33.55 mmol) of 2-fluoro-6-octyloxypyridine-3-boronic acid. ##STR22##

Provenance & Evidence