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Structure of 1197989-83-5

Chemical Structure| 1197989-83-5

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Product Details of [ 1197989-83-5 ]

CAS No. :1197989-83-5
Formula : C24H30B2O5
M.W : 420.11
SMILES Code : CC1(C)C(C)(C)OB(C2=CC=C(OC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C35)C5=C2)O1
MDL No. :MFCD28396385
InChI Key :IALWSEKANFQUBL-UHFFFAOYSA-N
Pubchem ID :57968038

Safety of [ 1197989-83-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1197989-83-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1197989-83-5 ]

[ 1197989-83-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 10016-52-1 ]
  • [ 1197989-83-5 ]
YieldReaction ConditionsOperation in experiment
31% With potassium acetate;PdCl2(PPh3)2; In dimethyl sulfoxide; Example 10 Synthesis of Compound 5 To a 20 mL DMSO solution of <strong>[10016-52-1]2,8-dibromodibenzofuran</strong> (1 g, 3.07 mmol) was added bispinacolatiodiboron (1.74 g, 6.75 mmol), KOAc (2 g, 21 mmol) and PdCl2(PPh3)2 (149 mg, 0.21 mmol), and the solution was stirred at 80° C. for 24 h. The catalyst was removed by filtration and washed with CH2Cl2 after the reaction mixture was cooled to room temperature. The filtrate was then washed with de-ionized H2O (50 mL) for five times, and the organic layer was dried over Mg2SO4, filtrated, concentrated and purified by column chromatography on silica gel (hexane/EtOAc=10:1) to give 2,8-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzofuran (0.4 g, 31percent). 1H NMR (400 MHz, CDCl3) delta 8.51 (s, 2H), 7.92 (d, 2H), 7.57 (d, 2H), 1.40 (s, 24H).
  • 2
  • [ 10016-52-1 ]
  • [ 73183-34-3 ]
  • [ 1197989-83-5 ]
YieldReaction ConditionsOperation in experiment
64.4% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 120℃; 2,8-Diboronic ester dibenzofuran was synthesized according to the synthetic method of previous research [25]. Crude product was purified by column chromatography (dichloromethane:n-haxane (1:4) andcomplete drying afforded a white product (12.2 g, 64.4% yield).
31% With potassium acetate;bis-triphenylphosphine-palladium(II) chloride; In dimethyl sulfoxide; at 80℃; for 24h; To a 20 mL DMSO solution of <strong>[10016-52-1]2,8-dibromodibenzofuran</strong> (1 g, 3.07 mmol) was added bispinacolatiodiboron (1.74 g, 6.75 mmol), KOAc (2 g, 21mmol) and PdCl2(PPh3)2 (149 mg, 0.21 mmol), and the solution was stirred at 80 C. for 24 h. The catalyst was removed by filtration and washed with CH2Cl2 after the reaction mixture was cooled to room temperature. The filtrate was then washed with de-ionized H2O (50 mL) for five times, and the organic layer was dried over Mg2SO4, filtrated, concentrated and purified by column chromatography on silica gel (hexane/EtOAc=10:1) to give 2,8-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzofuran (0.4 g, 31%). 1H NMR (400 MHz, CDCl3) delta 8.51 (s, 2H), 7.92 (d, 2H), 7.57 (d, 2H), 1.40 (s, 24H).
21.9 g With potassium acetate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine; In 1,4-dioxane; for 24h;Reflux; <strong>[10016-52-1]2,8-dibromodibenzofuran</strong> (20 g, 61.35 mmol) And bis (pinacol) diboron (38.95 g, 153.37 mmol), Potassium acetate (30.1 g, 306.7 mmol) was added to a round bottom flask And the mixture was dissolved in 500 mL of dioxane and refluxed. 705 mg (1.22 mmol) of bis (dibenzylidineacetone) palladium (0) (705 mg, 1.22 mmol) and tricyclohexylphosphine (PCy3, 668 mg, 2.45 mmol) were dissolved in 30 mL of dioxane and stirred for 30 minutes Respectively. After refluxing for 24 hours, it was cooled, filtered, and then 500 mL of water was added. The mixture was extracted three times with 300 mL of toluene, and the organic layer was concentrated under reduced pressure. Column chromatography afforded Intermediate 1 (21.9 g, 52.2 mmol).
  • 3
  • [ 7089-68-1 ]
  • [ 1197989-83-5 ]
  • C36H20N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% 2.0 g (4.8 mmol) of 2,8-bis (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) dibenzofurane,1,10-phenanthroline2.3 g (10.6 mmol) of28 mL of dioxane and 13 mL of 2M potassium phosphate aqueous solution were put into a 100 mL round bottom flask,Bubbling was carried out using argon for 20 minutes and after a predetermined time,0.266 g (0.29 mmol) of tris (dibenzylideneacetone) palladium (0)1.0 mL (0.696 mmol) of a 20percent tricyclohexylphosphine toluene solution was added.The reaction vessel was reacted by irradiating microwave (2.45 GHz, 150 W) for 2 hours. After the reaction,Dichloromethane was added to the reaction mixture to separate into an aqueous layer and an organic layer. The aqueous layer was extracted, and the solution obtained by extraction and the organic layer were combined and washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution. The organic layer was dried by adding anhydrous magnesium sulfate, and the obtained mixture was treated in the order of celite (manufactured by Wako Pure Chemical Industries, Ltd., catalog number: 531-16855, all in this embodiment), alumina and celite Laminated filtrationFollowed by filtration through an aid. Further, the mixture was washed with 2 L of ethyl acetate, and the obtained filtrate was concentrated to obtain a solid. Ethyl acetate was added to the obtained solid, irradiated with ultrasonic waves, and subjected to suction filtration to obtain 0.75 g of the target white solid, and the yield was 30percent. For microwave irradiation, a microwave synthesizer (manufactured by CEM, Discover) was used.The synthesis scheme (c-4) of Step 2 is shown below.
 

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