preparation | naphthylpentane -5-boric acid preparation is as follows: 11.7g of commercial 5-bromoacenaphthene is dissolved in 50ml of anhydrous toluene and 50ml of anhydrous ether mixed solvent, and the obtained solution is cooled to -40°C under argon atmosphere. A hexane solution of 35ml of 1.6M n-butyl lithium was added dropwise to the resulting solution, and the temperature was subsequently raised to -10°C. After 2 hours, the resulting solution was cooled to -70°C, and then another solution prepared by dissolving 35ml of triisopropoxyborane in 50ml of ether was added dropwise to the solution. The resulting solution was stirred for 3 hours at -70°C and then left to stand overnight. After one night, the solution obtained was acidified with 10% weight of dilute hydrochloric acid and the organic layer was extracted with toluene. The organic layer is washed with dilute hydrochloric acid and saturated sodium chloride solution, dried by anhydrous sodium sulfate, and the organic solvent is distilled with an evaporator. The residue was crystallized using toluene/hexane to obtain 4.5g (yield 45%) naphthol-pentane-5-boronic acid. |