Synthesis method of s-triazine boronic acid pinacol ester
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A synthesis method and technology of boric acid, which are applied in chemical instruments and methods, compounds containing elements of group 3/13 of the periodic table, organic chemistry, etc., can solve problems affecting the performance of photoelectric materials, failure to obtain final products, and difficulties in the preparation of boric acid, etc. , to achieve the effect of simple and effective treatment, thorough response and cost reduction
Active Publication Date: 2020-08-04
PUYANG HUICHENG ELECTRONICS MATERIAL
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Problems solved by technology
The first method introduces a heavy metal catalyst, and trace residues in the photoelectric material will affect the performance of the photoelectric material
The second method is limited by the activity of the triazine ring, and the preparation of the corresponding boronic acid is relatively difficult and the yield is low
At the same time, when boric acid and pinacol are dehydrated into esters under the condition of THF with strong water solubility, it is easier to remove a molecule of water and cause the final product to be unable to be obtained. Reaction with pinacol, in this way, boric acid needs to be taken out from the reaction solution, which will cause a certain loss
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Embodiment 1
[0016] (1) Put 38.83g (0.1mol) of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine and 260mL of tetrahydrofuran into the reactor, stir until completely dissolved, Add 85 mL of diethoxymethane, replace with nitrogen for 30 minutes, pass through liquid nitrogen, use an anhydrous ethanol bath to lower the temperature of the reaction system to below -90°C, and slowly add n-butyl lithium in n-hexane dropwise through a constant pressure funnel while maintaining this temperature Solution 50mL (2.5mol / L), keep this temperature for 30min after adding, then slowly add 18.18g of trimethyl borate dropwise through constant pressure funnel, keep this temperature for 30min after adding, naturally warm to room temperature. Add dilute hydrochloric acid with a mass percentage of 15% to adjust the pH to 6-7, separate the water layer, extract the water layer with ethyl acetate twice, each time with 15 mL, combine the organic layers, and dry the organic layer with anhydrous magnesium sulfate for 1 h ...
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Abstract
The invention relates to a synthesis method of s-triazine boronic acid pinacol ester, particularly discloses a synthesis method of a photoelectric material intermediate, namely 2, 4-diphenyl-6-[4-(4,4, 5, 5-tetramethyl-1, 3, 2- dioxaborolane -2-yl) phenyl]-1, 3, 5-triazine, and belongs to the field of organic chemical synthesis. According to the method, 2-(4-bromophenyl)-4, 6-diphenyl-1, 3, 5-triazine is used as a raw material to obtain an intermediate, and then the intermediate reacts with pinacol to obtain the target compound. In the synthesis of the intermediate, the reaction temperature is reduced to -90 DEG C, and meanwhile, diethoxymethane is adopted to reduce the activity of a solvent, so that halogen lithium exchange directionally occurs in the reaction; when the pinacol ester issynthesized, a one-pot method is adopted, and a molecular sieve is added, so that the effect of synthesizing the pinacol ester through dehydration at a relatively low temperature is achieved, and industrial production is facilitated.
Description
technical field [0001] The invention belongs to the field of organic chemical synthesis and relates to photoelectric material intermediate 2,4-diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxolane The synthetic method of borane-2-yl)phenyl]-1,3,5-triazine. Background technique [0002] Generally speaking, in organic electroluminescent devices (OLED), the introduction of s-triazine structure can effectively improve the electron injection performance and thermal stability of optoelectronic materials. It is often used in electron transport materials and also in light-emitting materials, especially blue color organic electroluminescent materials. The structure of s-triazine is symmetrical in space, the ring is easy to be modified by other groups, and has strong electron transport ability, so this kind of compound is widely used in various organic electroluminescent devices. [0003] Boric acid pinacol ester adopts two kinds of methods more in synthesis, and one is under the effec...
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