Tetrahydrofuran → 4-Methyl-1-naphthaleneboronic acid

Participants

Reaction Conditions

Reaction Steps

To a 125 mL round-bottomed flask equipped with N2 inlet were added 1.78 g (11.4 mmol) 1-bromo-4-methylnaphthalene and 20 mL dry tetrahydrofuran. The solution was cooled to −70° C., and 5.49 mL (13.7 mmol) of a 2.5M solution of n-butyl lithium in hexane was added over 5 minutes, and the reaction stirred at −70° C. for 10 minutes. The solution was then treated with 2.34 mL (13.7 mmol) triethyl borate, stirred 5 minutes at −70° C., then warmed to room temperature and stirred 40 hours. The reaction was quenched with aqueous ammonium chloride solution, poured into 0.5 N hydrochloric acid, and extracted into ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and evaporated to a white solid after trituration with hexane, mp 224-228° C., 1.9 g (90%).

Provenance & Evidence