Preparation background and overview of pinacol 1-naphthylboronic acid ester
1-Naphthylboronic acid pinacol ester is an organic raw material that can be used to participate in the Suzuki reaction. 1-Naphthylboronic acid pinacol ester can be prepared in one step from 1-bromonaphthalene and diboronic acid pinacol ester.
Preparation of 1-naphthylboronic acid pinacol ester
Preparation report 1 of pinacol 1-naphthylboronic acid ester,
Stannous fluoroborate
In a 250mL three-necked flask, add nitrogen, add 0.02mol 1-bromonaphthalene and dissolve it in 100ml tetrahydrofuran (methoxypyridine THF), then add 0.024mol pinacol diborate, 0.0002mol (1,1′ -Bis(diphenylphosphine)ferrocene)dichloropalladium(II) and 0.05mol potassium acetate were added, the mixture was stirred, and the mixed solution of the above reactants was heated to reflux at the reaction temperature of 80°C for 5 hours; after the reaction was completed, Cool and add 100 ml water, and the mixture is filtered and dried in a vacuum oven. The obtained residue was separated and purified through a silica gel column to obtain 1-naphthylboronic acid pinacol ester; the HPLC purity was 99.9% and the yield was 92.7%. Elemental analysis structure (molecular formula C16H19BO2): theoretical value: C, 75.62; H, 7.54; B, 4.25; O, 12.59; test value: C, 75.66; H, 7.55; B, 4.27; O, 12.63. ESI-MS(m/z)(M+): The theoretical value is 254.14, and the measured value is 254.22.
Preparation report 2 of pinacol 1-naphthylboronic acid ester,
Dissolve 2.07g (10mmol) of 1-bromonaphthalene in 30mL of THF, and then add 4mL of n-butyllithium (2.5M in n-hexane) at -78°C. After 1 hour at the same temperature, 2.0 mL (10 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane was added to the mixture. The resulting mixture was stirred at room temperature for 5 hours, and then, after adding water thereto, it was washed three times with 30 mL of diethyl ether. The diethyl ether layer obtained therefrom was dried using MgSO4 and then dried again under reduced pressure to obtain the product. The product was separated and purified by column chromatography to obtain 1.96 g (yield: 77%) of 1-naphthylboronic acid pinacol ester.
References
[1] [Chinese invention] CN201910242573.8 An organic compound based on azabenzene and its application in OLED
[2] [China invention, China invention authorization] CN201510088632.2 Fused ring compound and organic light-emitting device containing the same
