Tetracene derivative, preparation method and application thereof
A tetracene and reaction technology, applied in the field of tetracene derivatives and their preparation, can solve the problems of retention, difficulty in selective modification of even-numbered paracyclic compounds, and achieve low cost, shortened preparation time, and improved synthesis efficiency Effect
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[0105] Compound 2,8-dibromotetracene, the preparation method comprises the following steps:
[0106] 1) Put compound 2-amino-5-bromobenzoic acid, a kind of acid 1 and nitrous acid compound in solvent 1, react at low temperature for 0.1-300h, wait for a large amount of organic diazonium salt to precipitate, add diethyl ether and then After stirring for 0.1-300h, filter. Collect the filtered organic diazonium salt, place it together with furan in another solvent 2, heat to reflux for 0.1-300 h, and wait until the solution is clarified to complete the reaction. After post-treatment, the product 6-bromo-1,4-epoxy-1,4-dihydronaphthalene was obtained.
[0107] 2) Put the compound 6-bromo-1,4-epoxy-1,4-dihydronaphthalene, 4-bromobenzocyclobutane and an additive 1 in the solvent 3, and heat to reflux for 0.1 to 300h to end the reaction . After post-treatment, the product 2,8-dibromo-5,12-epoxy-5,5a,6,11,11a,12-hexahydrotetracene was obtained with a yield of 1-99%.
[0108] 3) Put ...
Embodiment 1
[0117] a) 6-bromo-1,4-epoxy-1,4-dihydronaphthalene
[0118]
[0119] In a 1000 mL two-neck round bottom flask with a dropping funnel, add 2-amino-5-bromobenzoic acid (63.5 g, 294 mmol) and 400 mL of ethanol, then put it into a cooling bath to stir and cool down to -10°C. Hydrochloric acid (24.5 mL, 294 mmol) was slowly added dropwise into the two-neck round bottom flask, and after the solid was completely dissolved, isoamyl nitrite (35 g, 294 mmol) was slowly added dropwise into the flask. During the dropwise addition, the solution turned from yellow to brown with a small amount of bubbles. After a period of reaction, the solution gradually changed from clear to cloudy. At this point 500 mL of anhydrous diethyl ether was added and stirring was continued at <10°C for a period of time. After the reaction was completed, the round-bottomed flask was carefully sonicated and filtered, and the solid was washed three times with anhydrous ether (200 mL), and then the obtained soli...
Embodiment 2
[0127]
[0128] In a 100mL two-necked round-bottomed flask with a reflux condenser, sequentially add 2,8-dibromotetracene (1.0g, 2.6mmol) prepared in Example 1 above, phenylboronic acid (0.95g, 7.8mmol), phosphoric acid Potassium monohydrate (3.0 g, 13 mmol) and toluene (30 mL). To this suspension were added 12 mg palladium acetate (0.05 mmol) and 41 mg SPhos (0.1 mmol), and the reaction mixture was heated at reflux for more than 16 h. After the reaction, stop stirring and cool to normal temperature, then add 50mL of petroleum ether to the reaction system, and place the two-neck round-bottomed flask in an ultrasonic oscillator for a period of time. The mixture in the round bottom flask was filtered with a suction funnel to obtain a reddish brown solid. The crude product was washed successively with 50 mL of ethanol, 100 mL of hot water, 50 mL of methanol, 50 mL of ether and 50 mL of n-hexane to finally obtain a brick red solid (0.98 g, yield 99%). HRMS Calcd.for C 30 h ...
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