Hydrochloric Acid → 4-(9H-Carbazol-9-yl)phenylboronic Acid

Participants

Reaction Conditions

Reaction Steps

19.6 g (60.7 mmol) of N-(4-bromophenyl)carbazole synthesized in Step 1 of Example 3 was put into a 500 mL three-neck flask, and the atmosphere in the flask was substituted by nitrogen. 100 mL of tetrahydrofuran (THF) was added to the flask and cooled to −78° C. Into this solution, 66.8 mL (42.3 mmol) of n-butyllithium hexane solution (1.58 mol/L) wad dropped under a nitrogen gas flow, and the solution was stirred at the same temperature for three hours. Then, 13.5 mL (140 mmol) of trimethyl borate was added into this solution at the same temperature, and while the temperature of the solution was being increased to room temperature, the solution was stirred for about 24 hours. About 200 mL of 2.0 mol/L hydrochloric acid was added into this solution and stirred at room temperature for one hour. This solution was extracted with ethyl acetate and the extracted solution and an organic layer were washed together with a saturated brine and dried with magnesium sulfate. The mixture was filtrated, and the filtrate was concentrate to obtain a solid substance. The obtained solid substance was recrystallized with a mixed solvent of chloroform and hexane, so that 10.2 g of the white powder of 4(9H-carbazol-9-yl)phenylboronic acid was obtained in yield 58%.

Provenance & Evidence