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CAS No. : | 1592-95-6 | MDL No. : | MFCD00222621 |
Formula : | C12H8BrN | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | LTBWKAYPXIIVPC-UHFFFAOYSA-N |
M.W : | 246.10 | Pubchem ID : | 252446 |
Synonyms : |
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Chemical Name : | 3-Bromo-9H-carbazole |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | |
Hazard Statements: | H315-H319 | 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 N2;tris-(dibenzylideneacetone)dipalladium(0); Pd2(dba)3; In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; hexane; dichloromethane; toluene; | A mixture of 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (12 g, 32.5 mmol), 3-bromo-9H-carbazole (6.66 g, 27.1 mmol), and potassium phosphate (34.5 g, 162 mmol) in 500 mL of toluene and 50 mL of H2O was bubbled with N2 for 20 min. Dicyclohexyl(2',6'-dimethoxybiphenyl-2-yl)phosphine (0.445 g, 1.083 mmol) and Pd2(dba)3 (0.248 g, 0.271 mmol) were then added, and the mixture was heated to reflux under N2 for 5 h. TLC indicated the reaction was done. The reaction was extracted with dichloromethane and washed with brine and dried with magnesium sulfate. The solution was heated up to boil. Hexane was added. The dichloromethane was boiled off and hexanes volume reached about 1200 mL. Precipitate formed during boiling off dichloromethane. The solution was cooled to room temperature and stirred overnight. The precipitate was filtered and dissolved in THF and ran a short silica gel plug. After dried under vacuum at 60 C., 9.6 g (87%) of product was obtained. Synthesis of Compound 1. A mixture of <strong>[5408-56-0]2-iododibenzo[b,d]furan</strong> (2.59 g, 8.81 mmol), 9-phenyl-9H,9'H-3,3'-bicarbazole (3 g. 7.34 mmol), and sodium t-butoxide (1.764 g, 18.36 mmol) in 200 mL of xylene was bubbled with N2 for 20 min. Dicyclohexyl(2',6'-dimethoxybiphenyl-2-yl)phosphine (0.121 g, 0.294 mmol) and Pd2(dba)3 (0.067 g, 0.073 mmol) were then added, and the mixture was heated to reflux under N2 for 24 h. The mixture was cooled and filtered through Celite. After solvent evaporation, the residue was coated on Celite and purified by column chromatography 3.7 g of product was obtained after column. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.6% | With copper(l) iodide; caesium carbonate; ethylenediamine; In toluene; for 12h;Reflux; | After introducing 9H-carbazole (20 g, 119.6 mmol), 3-bromo-9H-carbazole (35.3 g, 143.5 mmol), copper(I) iodide (59.8 g, 59.8 mmol), cesium carbonate (97.4 g, 229 mmol), ethylene diamine (7.18 g, 119.6 mmol), and toluene(600 mL) into a flask, the mixture was stirred under reflux for 12 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate, washed with purified water, dried with anhydrous MgSO4, and distilled under reduced pressure. The residues were purified by column chromatography to obtain compound 2-1 (31.6 g, yield: 79.6%) |
79.6% | With copper(l) iodide; caesium carbonate; ethylenediamine; In toluene; at 20℃; for 12h; | 9H-carbazole (20 g, 119.6 mmol),3-Bromo-9H-carbazole(35.3 g, 143.5 mmol),Copper (I) Iodide(59.8 g, 59.8 mmol),Cesium carbonate (97.4 g, 229 mmol),Ethylenediamine (7.18 g, 119.6 mmol) And 600 mL of toluene, and the mixture was stirred under reflux for 12 hours.Cooled to room temperature, extracted with ethyl acetate, and washed with purified water. Dried over anhydrous magnesium sulfate, and distilled under reduced pressure. The resulting residue was subjected to column chromatography to obtain Compound 2-1 (31.6 g, yield 79.6%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With potassium phosphate; copper(l) iodide; (1R,2R)-1,2-Dimethyl-cyclohexane; In 1,4-dioxane; for 14h;Inert atmosphere; Reflux; | The bottom of argon atmosphere, <strong>[5408-56-0]2-iododibenzofuran</strong> 38g (154mmol), 45.4 g (154mmol) of 3-bromocarbazole, the copper iodide 8.8g (46.3mmol), 17.6 g (154mmol) of trans-1,2-cyclohexanediamines and the tripotassium phosphate 68.8g (324mmol) were added to 700 ml of drying 1,4-dioxane, and heating-at-reflux stirring was carried out for 14 hours. 500 ml of tetrahydrofurans were added and agitated to the residue produced by condensing under decompression of a reaction solution, and the insoluble matter was filtered through silica gel. By dissolving the residue produced by condensing under decompression of filtrate in toluene, and refining with silica gel column chromatography (toluene 100%), the intermediate field G38g (59% of yield) were obtained as a white solid |