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CAS No. : | 90-90-4 | MDL No. : | MFCD00000103 |
Formula : | C13H9BrO | Boiling Point : | - |
Linear Structure Formula : | C6H5C(O)C6H4Br | InChI Key : | KEOLYBMGRQYQTN-UHFFFAOYSA-N |
M.W : | 261.11 | Pubchem ID : | 7030 |
Synonyms : |
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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: |
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* 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 |
---|---|---|
1.0 g of <strong>[902518-11-0]9-(2-bromophenyl)-9H-carbazole</strong> as the intermediate of preparation example 8 was dissolved in 10 mL of purified tetrahydrofuran, and the resulting solution was cooled to -78 degree C, and 1.613 mL of butyllithium was slowly added dropwise. The mixture was stirred at the same temperature for 30 min, and 1.05 g of 4-bromobenzophenone was added. The mixture was stirred at the same temperature for 40 minutes, and then further stirred at room temperature for an additional 3 hours. The reaction was terminated with aqueous ammonium chloride, and the reaction mixture was extracted with ethyl ether. The organic layer was dewatered using anhydrous magnesium sulfate, and the organic solvent was then removed. The resulting solid was then dispersed in ethanol, stirred for one day, filtered and vacuum dried, thus obtaining an intermediate material. The solid thus obtained was dispersed in 10 ml of acetic acid, and 10 drops of concentrated sulfuric acid were added, after which the mixture was refluxed for 4 hours. The resulting solid was filtered, washed with ethanol, and vacuum dried, yielding 8-(4-bromophenyl)-8-phenyl-8H-indolo-[3,2,1-de]acridine compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With oxygen; copper diacetate; potassium carbonate; aniline; In dimethyl sulfoxide; at 120℃;Schlenk technique; Sealed tube; | General procedure: An oven-dried Schlenk tube was charged with a magnetic stir-bar, 1,2-diarylalkynes 1 (0.5mmol), aniline (0.6mmol), K2CO3 (0.5mmol), Cu(OAc)2 (0.075mmol), DMSO (3mL), The tube was sealed, and oxygen was purged through syringe. Reaction was stirred at 120C for 16-18h. After the reaction was finished, the reaction mixture was diluted in 30mL ethyl acetate, filtered on Celite pad. The organic portion was washed with a saturated solution of brine (8mL), saturated NH4Cl (8mL), a saturated solution of brine (8mL), dried (Na2SO4) and concentrated in vacuum, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to afford the desired products 2. |
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