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CAS No. : | 1660996-72-4 | MDL No. : | N/A |
Formula : | C50H64B4O8 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IMKQIUDDYPXPIU-UHFFFAOYSA-N |
M.W : | 836.28 | Pubchem ID : | 134821676 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 110℃; for 72h;Inert atmosphere; | Mixture of 1 (3 g, 4.63 mmol), potassium acetate (4.56 g, 46.50 mmol), bis(pinacolato)diboron(5.30 g, 20.4 mmol), and anhydrous dioxane (90 mL) was put into a three-neckedflask and argon gas was bubbled for 30 min. [1,10-Bis(diphenylphosphino)ferrocene]dichloropalladium (II) in dichloromethane (180 mg, 0.22 mmol) were added to the flaskunder argon. The mixture was charged with argon gas for 30 min and then stirred at110 C for 3 days. After cooling to room temperature, the reaction mixture was pouredinto cold water. The precipitate was isolated by filtration and dried in a vacuum oven.The residue was dissolved in chloroform and purified by column chromatography (eluent:chloroform: ethyl acetate 1:1). The resulting white solid was washed with methanol anddried (yield 3.16 g, 82%). 1H NMR (300MHz, CDCl3) 7.5 (8H, d), 7.0 (8H, d) ppm, 1.3(24H, s) ppm. FT-IR (KBr pellet, cm1): 2981 (C-H), 1606 (CC), 1359 (B-O). |
75% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,2-dimethoxyethane; at 100℃; for 12h;Inert atmosphere; | A mixture of tetrakis(4-bromophenyl)ethene(0.65 g, 1.0 mmol), bis(pinacolato)diboron (1.50 g, 6.0 mmol), 1,10 -bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethanecomplex (Pd(dppf)Cl2CH2Cl2) (0.041 g, 0.05 mmol), and potassiumacetate (KOAc) (1.60 g, 16.0 mmol) in 30 mL degassed 1,2-dimethoxyethane (DME) was heated to 100 C for 12 h under N2. Aftercooling down, the solvent was removed in vacuum, and the residue wassubjected to chromatography on a silica gel column using chloroform aseluent. Repeated column chromatography and the following recrystallizationfrom chloroform and methanol afforded the target white compoundTMDB-TPE (0.63 g, yield 75.0%). 1H NMR (400 MHz, CDCl3-d):7.50 (d, 8H, J 8.00 Hz), 6.99 (d, 8H, J 8.00 Hz), 1.32 (s, 48H).MALDI-TOF MS: an isotopic cluster peaking at m/z 836.4, Calcd. forC50H64B4O8, [M] 836.5. Anal. Calcd. for C50H64B4O80.4CHCl3: C,68.47; H, 7.34. Found: C, 68.43; H, 7.18. |
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