1100752-07-5|9-(8-Bromodibenzo[b,d]furan-2-yl)-9H-carbazole| Ambeed

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CAS No. :	1100752-07-5
Formula :	C₂₄H₁₄BrNO
M.W :	412.28
SMILES Code :	BrC1=CC=C(OC2=CC=C(N3C4=C(C5=C3C=CC=C5)C=CC=C4)C=C26)C6=C1
MDL No. :	MFCD30343561
InChI Key :	CXUDTGWLYIMSKM-UHFFFAOYSA-N
Pubchem ID :	57544042

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Yield	Reaction Conditions	Operation in experiment
61%	With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 140℃; for 6h;	To a 250 mL reaction flask, 1.0 mmol of <strong>[10016-52-1]2,8-dibromodibenzofuran</strong>, 1.1 mmol of carbazole, 0.06 mmol of dppf, 0.02 mmol of Pd (OAc)2, 1.2 mmol of t-BuONa and 30 mL of xylene, and then heated to 140 C for 6 hours.30 mL of ethyl acetate and 30 mL of water were added to the system, stirred and the aqueous phase was extracted twice with 30 mL of ethyl acetate. The organic phase was washed twice with 30 mL of saturated brine and the organic phases were combined and spin dried to give a yellow solid.A silica gel column, petroleum ether: ethyl acetate = 6: 1 was leached to give a white solid product in a yield of 61%.
40%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 100℃; for 32h;Inert atmosphere;	In a nitrogen environment 9H-carbazole(100 g, 598 mmol) was dissolved in 2,000 mL of toluene, where the <strong>[10016-52-1]2,8-dibromodibenzofuran</strong>(292 g, 897 mmol), tris(diphenoquinone alkylpiperidinyl) dipalladium (o) (5.48 g, 5.98 mmol), tris-tertbutylphosphine(6.05 g, 29.9 mmol) and sodium tert-butoxide(69.0 g, 718 mmol) sequentially into heating by and it refluxed during100 C in 32 hours . After the reaction was completed, the reaction solution into water and extracted with dichloromethane (DCM) and then water was removed with anhydrous MgSO4, filter and was concentrated under reducedpressure. Thus separated and purified the resulting residue was purified by flash column chromatography compounds to obtain a I-7(98.6 g, 40%)
30%	With 18-crown-6 ether; copper; potassium carbonate; In 1,2-dichloro-benzene; at 50 - 200℃; for 45.75h;Inert atmosphere;	Example 1.8.12 9-(8-bromodibenzo[b,d]furan-2-yl)-9H-carbazole (Compound 12) A mixture of carbazole (1.15 g, 6.87 mmol), <strong>[10016-52-1]2,8-dibromodibenzo[b,d]furan</strong> (4.48 g, 13.74 mmol), copper powder (0.30 g, 4.58 mmol), potassium carbonate (3.80 g, 27.50 mmol), 18-crown-6 (0.61 g, 2.29 mmol), and 1,2-dichlorobenzene (50 mL) was degassed with bubbling argon for 45 min at 50 C. The reaction mixture was then heated to 200 C. and was stirred overnight (45 hours), maintaining an argon atmosphere. Production of decoupled material was shown by LCMS and the reaction was cooled to room temperature. The mixture was filtered, and the filtrate was dried. The copper was removed by a short silica gel plug with dichloromethane as the eluent, and the product was purified by silica gel column chromatography with toluene in hexanes as the eluent. The product fractions were then dried and the product was collected to yield Compound 12 (0.861 g, 30%).

15%	With copper; potassium carbonate; In N,N-dimethyl acetamide; at 135 - 137℃; for 16h;Inert atmosphere;	6.29 g (0.0193 mol) of 2,7-dibromodibenzofuran,2.9 g (× 0.9 mol) of carbazole,4.0 g (× 1.5 mol) of potassium carbonate, 3.68 g (× 3 mol) of Cu powder and 75 ml of dry DMAc were mixed and stirred under a nitrogen stream for 16 hours (internal temperature 135 to 137 C.).The insoluble matter was filtered under reduced pressure, the filtrate was extracted with THF, and the solvent was removed by distillation under reduced pressure. Purification by column chromatography (packing agent: silica gel, developing solution: toluene / n-hexane) gave 1.2 g of exemplified compound 5-1. Yield 15%
6.4 g	With palladium diacetate; sodium t-butanolate; In toluene;Reflux;	A round bottom flask was dissolved in 5 g of 2,8-DIBROMODIBENZOFURAN (subA), 7.3 g of 9H-carbazole (sub2), 5.5 g of t-BuONa, 0.5 g of Pd (OAC) 2, and 50 ml of toluene, followed by stirring under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with MC, filtered under reduced pressure, and then purified by column and recrystallized to obtain 6.4 g (yield 50%) of intermediate 9-(8-bromodibenzo[b,d]furan-2-yl)-9H-carbazole.Sub C2 to sub C22 were synthesized as shown in Table 1 by varying starting materials Sub A and Sub B in the same manner as in sub C1.

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CAS No.: 1100752-07-5

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CAS No.: 1100752-07-5

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Code	Phrase
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