Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 36847-10-6, name is 4,6-Dibromopyrimidine. A new synthetic method of this compound is introduced below., HPLC of Formula: C4H2Br2N2
Synthesis Example 1 (0304) In this example, a method of synthesizing 9,9?-[pyrimidine-4,6-diyl bis(biphenyl-3,3?-diyl)]bis(9H-carbazole) (abbreviation: 4,6mCzBP2Pm) (the structural formula (100)), which is a heterocyclic compound of one embodiment of the present invention, is described. The structure of 4,6mCzBP2Pm is shown below. Synthesis of 4,6mCzBP2Pm (0305) First, 0.54 g (2.3 mmol) of 2,4-dibromopyrimidine, 1.8 g (5.0 mmol) of 3-(3-(9H-carbazol-9-yl)phenyl)phenyl boronic acid, and 69 mg (0.23 mmol) of tris(2-methylphenyl)phosphine were put into a 50-mL three-neck flask, and the air in the flask was replaced with nitrogen. (0306) Then, 4.9 mL of a 2M potassium carbonate aqueous solution, 12 mL of toluene, and 4 mL of ethanol were added to this mixture, and the mixture was degassed by being stirred under reduced pressure. To this mixture, 10 mg (0.045 mmol) of palladium(II) acetate was added and stirring was performed under a nitrogen stream at 90 C. for 16 hours. After the stirring, water was added to the mixture, and an aqueous layer was subjected to extraction with toluene. (0307) The obtained solution of the extract and an organic layer were combined, and the mixture was washed with water and saturated brine. Then, the mixture was dried with magnesium sulfate. This mixture was separated by gravity filtration, and the filtrate was concentrated to give an oily substance. The oily substance was purified by silica gel column chromatography (as the developing solvent, first hexane and toluene in a ratio of 5:1 were used, and then chloroform and ethyl acetate in a ratio of 50:1 were used). The obtained fraction was concentrated to give an oily substance. Chloroform was added to this oily substance, the mixture was suction-filtered through Celite and alumina, and the filtrate was concentrated to give an oily substance. This oily substance was purified by high performance liquid column chromatography (HPLC) (developing solvent: chloroform). (0308) The obtained fraction was concentrated to give an oily substance. This oily substance was recrystallized with toluene/hexane to give 1.0 g of a target white solid in a yield of 63%. (0309) By a train sublimation method, 0.99 g of the obtained white solid was purified. In the purification by sublimation, the white solid was heated at 320 C. under the conditions where the pressure was 2.7 Pa and the argon flow rate was 5 mL/min. After the purification by sublimation, 0.91 g of a pale yellow solid was obtained at a collection rate of 92%. A synthesis scheme of the above synthesis method is shown in (A-1) below. (0310) Analysis results by nuclear magnetic resonance (1H-NMR) spectroscopy of the pale yellow solid obtained by the above-described synthesis method are described below. FIGS. 15A and 15B show the 1H-NMR chart. FIG. 15B is a chart where the range from 7 (ppm) to 10 (ppm) on the horizontal axis (delta) in FIG. 15A is enlarged. The results revealed that 4,6mCzBP2Pm (the structural formula (100)), which is a heterocyclic compound of one embodiment of the present invention, was obtained in this example. (0311) 1H-NMR (CDCl3, 300 MHz): g=7.30 (td, J=7.2 Hz, 1.2 Hz, 4H), 7.39-7.50 (in, 8H), 7.59-7.66 (m, 4H), 7.72 (t, J=7.8 Hz, 2H), 7.78-7.83 (m, 4H), 7.89 (s, 2H), 8.13-8.20 (in, 7H), 8.45 (s, 2H), 9.34 (sd, J=1.2 Hz, 1H).
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Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; SEO, Satoshi; KUBOTA, Yuko; TAKAHASHI, Tatsuyoshi; MITSUMORI, Satomi; (77 pag.)US2016/308139; (2016); A1;,
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