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CAS No. : | 1607-57-4 | MDL No. : | MFCD00000135 |
Formula : | C20H15Br | Boiling Point : | No data available |
Linear Structure Formula : | BrC(C6H5)C(C6H5)2 | InChI Key : | VUQVJIUBUPPCDB-UHFFFAOYSA-N |
M.W : | 335.24 | Pubchem ID : | 15354 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 12h;Inert atmosphere; Reflux; | TPE-OMe and TPE-SMe were prepared and synthesized by Suzuki-Miyaura cross-coupling reaction using triphenyl bromide as raw material.The general synthesis method is as follows:In the mixture of bromotristyrene (3.35g, 10.8mmol) and substituted phenylboronic acid (10.00mmol) was added K2CO3 aqueous solution (2M, 15mL),Ethanol (15mL) and toluene (50mL) and Pd(PPh3)4 (0.10g, 0.10mmol),The reaction was refluxed for 12h under the protection of nitrogen.After cooling to room temperature, the reaction mixture was poured into water,It was extracted three times with dichloromethane, and the organic layer was washed with brine,Then dry on MgSO4.After removing the solvent under reduced pressure, pass through silica gel column chromatography,Petroleum ether is used as the eluent to obtain a white solid powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.3% | With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In water; toluene; at 120℃; for 39h;Inert atmosphere; | under argon protection,Triphenylbromoethylene (168.1 mg, 0.47 mmol) was sequentially added to a 100 mL reaction flask.Tetrabutylammonium bromide (ie TBAB, 15.8 mg, 0.049 mmol),2-fluorophenylboronic acid (84.4 mg, 0.60 mmol), anhydrous potassium carbonate (207.8 mg, 1.50 mmol),Tetrakis(triphenylphosphine)palladium (29.9 mg, 0.026 mmol), 15 mL of toluene,5 mL water. Heat to reflux under stirring (oil bath temperature 120 C),Reaction for 35 h. After the reaction was monitored by TLC, the mixture was separated and the aqueous phase was extracted with dichloromethane (20 mL×2).The organic phases were combined, dried over anhydrous sodium sulfate, filtered and evaporated.Then, it was dissolved in 5 mL of dichloromethane and then subjected to thin layer chromatography (developing agent was n-hexane, specific shift value Rf=0.2), and the blue and white light band at 365 nm of ultraviolet light was scraped off, rinsed with dichloromethane, and the solvent was evaporated. ,A white solid 62.4 mg was obtained as Compound 1a, yield 37.6%, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; caesium carbonate; In water; toluene; for 24.0h;Inert atmosphere; | 5-Bromoisophthalaldehyde (1) and diformylphenylboronic ester (2)were prepared according to the previously reported procedure [23].Bromotriphenylethylene (1.34 g, 4.0 mmol), 2 (1.28 g, 4.8 mmol), tetrabutylammoniumbromide (0.03 g, 0.1 mmol) and Cs2CO3 (1.30 g, 4.0mmol) were dissolved in the mixture of toluene (40 mL) and H2O (5 mL).The reaction mixture was degassed and stirred under nitrogen atmospherefor 0.5 h, and then a catalytic amount of Pd(PPh3)4 (0.11 g, 0.1mmol) was added and refluxed for another 24 h. After being cooled toroom temperature, the solvent was removed under a vacuum. The crudeproduct was purified by column chromatography to get pale powder ofTPE-2CHO with a yield of 1.25 g (81%). 1H NMR (400 MHz, CDCl3): δ9.87 (s, 2H), 8.10 (t, J = 1.52 Hz, 1H), 7.78 (d, J = 1.56 Hz, 2H),7.17-7.09 (m, 9H), 7.05-7.00 (m, 6H). 13C NMR (100 MHz, CDCl3): δ191.0, 146.2, 143.8, 142.5, 142.4, 142.1, 138.2, 137.6, 136.6, 131.3,131.2, 131.0, 128.2, 128.2, 128.1, 127.8, 127.3, 127.2, 127.1. FT-IR(KBr pellets) v 3463 (s), 3076 (w), 3024 (w), 2835 (w), 2715 (w),1699 (s), 1593 (m), 1490 (m), 1442 (m), 1380 (m), 1137 (m), 1074 (w),964 (w), 889 (w), 777 (w), 761 (w), 700 (s), 650 (w), 632 (w), 576 (w).Anal. Calculated for C28H20O2: C, 86.56; H, 5.15%. Found: C, 86.47; H,5.34%. Single crystals suitable for X-ray diffraction measurements wereobtained in CH2Cl2 for a week. |
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