Hydrochloric Acid → Boronic acid, [4-[2-(phenylmethoxy)ethyl]phenyl]-

Participants

Reaction Steps

13.7 g (47.1 mmol) of 4-(2-benzyloxyethyl) phenylbromide and 80 ml of dry THF were cooled to -75° C., and 34.0 ml of n-butyllithium (1.65M) was dripped to it. Stirring at the foregoing temperature was performed for 3 hours, and then mixture solution of 12.9 g (68.7 mmol) of triisopropoxyboron and 50 ml of dry THF was dripped, and stirring at -75° C. was performed for 2 hours and that at room temperature was performed for 14 hours. After the reactions had been completed, 50 ml of 10% hydrochloric acid was added, and extraction with ethyl acetate was performed. After the extracted solution was dried, the solvent was removed by filtration. Then, refining was performed with a silica gel column chromatography (developing solvent: toluene/ethyl acetate=20/1) so that 8.62 g of 4-(2-benzyloxyethyl) phenyl boronic acid was obtained (yield 71%).

Provenance & Evidence