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Product Details of [ 186772-43-0 ]

CAS No. :186772-43-0 MDL No. :MFCD18089329
Formula : C10H12BrI Boiling Point : -
Linear Structure Formula :- InChI Key :QOBRAZDMDGZKHL-UHFFFAOYSA-N
M.W : 339.01 Pubchem ID :11461895
Synonyms :

Safety of [ 186772-43-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338-P304+P340 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 186772-43-0 ]

* 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.

  • Downstream synthetic route of [ 186772-43-0 ]

[ 186772-43-0 ] Synthesis Path-Downstream   1~49

  • 2
  • [ 186772-43-0 ]
  • [ 1066-54-2 ]
  • [ 144001-06-9 ]
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  • [ 89343-06-6 ]
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  • [ 863782-50-7 ]
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  • [ 186772-43-0 ]
  • [ 863782-54-1 ]
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  • [ 186772-43-0 ]
  • [ 863782-52-9 ]
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  • [ 186772-43-0 ]
  • [ 863782-53-0 ]
  • 7
  • [ 186772-43-0 ]
  • (2-{3-<i>tert</i>-butyl-5-[(triisopropylsilanyl)-ethynyl]-phenyl}-oxiranyl)-methanol [ No CAS ]
  • 8
  • [ 186772-43-0 ]
  • [ 863782-56-3 ]
  • 9
  • [ 186772-43-0 ]
  • [ 863782-55-2 ]
  • 10
  • [ 186772-43-0 ]
  • [ 863782-51-8 ]
  • 11
  • [ 186772-43-0 ]
  • C29H32 [ No CAS ]
  • 12
  • [ 186772-43-0 ]
  • [ 863782-58-5 ]
  • 13
  • [ 186772-43-0 ]
  • [ 863782-59-6 ]
  • 14
  • [ 186772-43-0 ]
  • C47H72Si2 [ No CAS ]
  • 15
  • [ 186772-43-0 ]
  • C47H72Si2 [ No CAS ]
  • 16
  • [ 186772-43-0 ]
  • C58H60 [ No CAS ]
  • 17
  • [ 769-92-6 ]
  • [ 186772-43-0 ]
  • 26
  • [ 186772-43-0 ]
  • [ 186772-55-4 ]
  • 28
  • [ 186772-43-0 ]
  • 1,1′-(5,5’‘-di-tert-butyl[1,1′:3′,1’‘-terphenyl]-3,3’‘-diyl)bis(2-iodo-3-methyl-1H-imidazol-3-ium) bis(trifluoromethanesulfonate) [ No CAS ]
  • 29
  • [ 186772-43-0 ]
  • 1-(3’‘,5-di-tert-butyl-5’‘-(3-methyl-1H-imidazol-3-ium-1-yl)[1,1′:3′,1’‘-terphenyl]-3-yl)-2-iodo-3-methyl-1H-imidazol-3-ium bis(trifluoromethanesulfonate) [ No CAS ]
  • 30
  • [ 186772-43-0 ]
  • 1,1′-(5,5’‘-di-tert-butyl[1,1′:3′,1’‘-terphenyl]-3,3’‘-diyl)bis(3-methyl-1H-imidazol-3-ium) bis(trifluoromethanesulfonate) [ No CAS ]
  • 31
  • [ 186772-43-0 ]
  • 1,1′-(5,5’‘-di-tert-butyl-[1,1′:3′,1’‘-terphenyl]-3,3’‘-diyl)bis(1H-imidazole) [ No CAS ]
  • 32
  • [ 186772-43-0 ]
  • 1,1′-(5,5’‘-di-tert-butyl[1,1′:3′,1’‘-terphenyl]-3,3’‘-diyl)bis(2-iodo-1H-imidazole) [ No CAS ]
  • 33
  • [ 186772-43-0 ]
  • 1-(3’‘,5-di-tert-butyl-5’‘-(1H-imidazol-1-yl)[1,1′:3′,1’‘-terphenyl]-3-yl)-2-iodo-1H-imidazole [ No CAS ]
  • 34
  • [ 288-32-4 ]
  • [ 186772-43-0 ]
  • 1-(3-bromo-5-(tert-butyl)phenyl)-1H-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.7% With copper(I) oxide; salicylaldehyde-oxime; caesium carbonate; In acetonitrile; at 50℃;Schlenk technique; Inert atmosphere; General procedure: Salicylaldoxime (0.2 equiv), imidazole (1.2 equiv), Cs2CO3 (2.0equiv), and Cu2O (0.1 equiv) were added to an oven driedSchlenk tube under an inert atmosphere (dry N2). A spargedsolution of <strong>[186772-43-0]1-bromo-3-(tert-butyl)-5-iodobenzene</strong> (8) (preparedby a known procedure (19)), or 1-bromo-3-iodobenzene(8a) (1 equiv, 0.8 M in total reaction mixture) dissolved in dryacetonitrile was then added to the Schlenk tube using a cannulaand the clear reaction mixture with Cu2O and Cs2CO3suspension was raised to 50 C in an oil bath and left to stirfor 25 h. The solution was then allowed to cool to rt beforediluting with DCM and filtering through diatomaceous earth.The product was then purified by flash column chromatographyusing normal phase silica, and/or by vacuum distillationat 1 Torr.
  • 35
  • [ 67-56-1 ]
  • [ 186772-43-0 ]
  • [ 1047661-27-7 ]
YieldReaction ConditionsOperation in experiment
75% With copper(l) iodide; 4,7-dimethoxy-1,10-phenanthroline; caesium carbonate; at 100℃; for 18h;Sealed tube; 9.0 g (27.2 mmol) of Intermediate 5-6 and 150 ml of methyl alcohol were mixed, and 0.5 g (2.7 mmol) of CuI, 17.7 g (54.5 mmol) of Cs2CO3, and 1.3 g (5.5 mmol) of 4,7-dimethoxy-1,10-phenanthroline were added thereto. The reaction mixture was stirred in a seal-tube at 100C. for 18 hours. After the reaction was completed, the reaction mixture was concentrated under reduced pressure, and the organic layer was extracted therefrom by using dichloromethane and water. The extracted organic layer was dried by using magnesium sulfate, distilled under reduced pressure, and purified by liquid chromatography to obtain 5 g (20.4 mmol, yield: 75%) of Intermediate 5-5. LC-MS m/z=244 (M+H)+.
  • 36
  • [ 186772-43-0 ]
  • [ 1047661-26-6 ]
  • 37
  • [ 186772-43-0 ]
  • C20H24Br2O [ No CAS ]
  • 38
  • [ 1047661-26-6 ]
  • [ 186772-43-0 ]
  • C20H24Br2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With 2-Picolinic acid; potassium phosphate; copper(l) iodide; In dimethyl sulfoxide; at 120℃; for 18h; 4.5 g (19.5 mmol) of Intermediate 5-4 and 7.0 g (19.5 mmol) of Intermediate 5-6 were mixed with 100 ml of DMSO, and 0.4 g (2.0 mmol) of CuI, 0.5 g (4.0 mmol) of picolinic acid, and 8.3 g (39.0 mmol) of K3PO4 added thereto. The reaction mixture was heated at a temperature of 120C. for 18 hours. After the reaction was completed, a saturated NaCl aqueous solution was added thereto to extract the organic layer. The extracted organic layer was dried by using magnesium sulfate, distilled under reduced pressure, and purified by liquid chromatography to obtain 5.5 g (12.7 mmol, yield: 65%) of Intermediate 5-3. LC-MS m/z=535 (M+H)+.
  • 39
  • [ 129316-09-2 ]
  • [ 186772-43-0 ]
YieldReaction ConditionsOperation in experiment
60% 17.7 g (60.47 mmol) of <strong>[129316-09-2]1,3-dibromo-5-(tert-butyl)benzene</strong> was mixed with 200 ml of diethyl ether, and n-BuLi (1.6 M in hexane) was slowly added thereto at a temperature of -78C. After the reaction mixture was stirred at a temperature of -78C. for 1 hour, 15 g (72.6 mmol) of iodine mixed with 20 ml of THF was slowly added by drops thereto. The reaction mixture was stirred at room temperature for 16 hours. After the reaction was completed, the organic layer was extracted by using ethyl acetate and a sodium thiosulfate aqueous solution, dried by using magnesium sulfate, distilled under reduced pressure, and purified by liquid chromatography to obtain 18 g (54.5 mmol, yield: 60%) of Intermediate 5-6. LC-MS m/z=291 (M+H)+.
  • 40
  • [ 186772-43-0 ]
  • C26H27N3O2 [ No CAS ]
  • 41
  • [ 186772-43-0 ]
  • C26H35BO4 [ No CAS ]
  • 42
  • [ 186772-43-0 ]
  • 3'-(tert-butyl)-6-ethyl-5'-(imidazo[1,2-a]pyrazin-3-yl)-N-(3-(trifluoromethyl)phenyl)-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • 43
  • methyl 4-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate [ No CAS ]
  • [ 186772-43-0 ]
  • C20H23BrO2 [ No CAS ]
  • 44
  • [ 62-53-3 ]
  • [ 186772-43-0 ]
  • C22H24N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; for 24h;Reflux; In a L reactor, 50 g (177 mmol) of <strong>[186772-43-0]1-bromo-3(tert-butyl)-5-iodobenzene</strong>,Aniline 36.2 g (389 mmol),1.6 g (7 mmol) of palladium acetate,51 g (530 mmol) of sodium tert-butoxide,Bis(diphenylphosphino)-1,1'-binaphthyl 4.4 g (7 mmol),500 mL of toluene was added, and the mixture was stirred under reflux for 24 hours.After completion of the reaction, the filtrate is concentrated by filtration,Separation by column chromatography gave 42.5 g of .Intermediate 3-a (Yield 50%)
50% With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; for 24h;Reflux; 1-Bromo-3(tert-butyl)-5-iodobenzene (50 g, 177 mmol), aniline (36.2 g, 389 mmol), palladium acetate (1.6 g, 7 mmol), sodium tert-butoxide (51 g, 530 mmol), bis(diphenylphosphino)-1,1?-binaphthyl (4.4 g, 7 mmol), and toluene (500 mL) were placed in a 1 L reactor. The mixture was refluxed with stirring for 24 h. After completion of the reaction, the reaction mixture was filtered. The filtrate was concentrated and purified by column chromatography to afford Intermediate 3-a (42.5 g, yield 50%).
  • 45
  • [ 186772-43-0 ]
  • C38H32N2O2 [ No CAS ]
  • 46
  • [ 186772-43-0 ]
  • C38H29BN2O2 [ No CAS ]
  • 47
  • [ 62-53-3 ]
  • [ 186772-43-0 ]
  • C38H32N2O2 [ No CAS ]
  • 48
  • [ 5599-71-3 ]
  • [ 186772-43-0 ]
  • C22H18BrCl2N [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tripotassium phosphate tribasic; copper (I) iodide; rac-diaminocyclohexane In 1,4-dioxane at 85℃; for 1.5h; Inert atmosphere; Intermediate 15-1 To a solution of 26.4 g (78.0 mmol) of Intermediate 7-1 in 250 mL of 1,4-dioxane was added 15.35 g (65.0 mmol) of 3,6-dichloro-9H-carbazole, 41.4 g (195.0 mmol) of potassium phos phate, 1.55 g (8.13 mmol) of copper iodide, 2.73 mL (22.75 mmol) of cyclohexane-1 ,2-diamine. The suspension was degassed with Ar, then heated to 85°C for 1.5 hours. After cooling to room temperature, the suspension was filtered over celite, rinsing with warm toluene (4x100 mL). The filtrate was evaporated, and the resulting residue was purified by silica-gel column chromatog raphy using heptanes as eluent. The resulting white solid was further recrystallized from cyclo hexane (2x150 mL) to give 14.66 g (80% yield) of Intermediate 15-1 as a white solid. 1H NMR (300 MHz, chloroform-o d 8.05 (dd, 2H), 7.67 (t, 1H), 7.50 (dt, 2H), 7.42 (dd, 2H), 7.32 (dd, 2H), 1.41 (s, 9H).
80% With tripotassium phosphate tribasic; copper (I) iodide; rac-diaminocyclohexane In 1,4-dioxane at 85℃; for 1.5h; Inert atmosphere; Intermediate 15-1 To a solution of 26.4 g (78.0 mmol) of Intermediate 7-1 in 250 mL of 1,4-dioxane was added 15.35 g (65.0 mmol) of 3,6-dichloro-9H-carbazole, 41.4 g (195.0 mmol) of potassium phos phate, 1.55 g (8.13 mmol) of copper iodide, 2.73 mL (22.75 mmol) of cyclohexane-1 ,2-diamine. The suspension was degassed with Ar, then heated to 85°C for 1.5 hours. After cooling to room temperature, the suspension was filtered over celite, rinsing with warm toluene (4x100 mL). The filtrate was evaporated, and the resulting residue was purified by silica-gel column chromatog raphy using heptanes as eluent. The resulting white solid was further recrystallized from cyclo hexane (2x150 mL) to give 14.66 g (80% yield) of Intermediate 15-1 as a white solid. 1H NMR (300 MHz, chloroform-o d 8.05 (dd, 2H), 7.67 (t, 1H), 7.50 (dt, 2H), 7.42 (dd, 2H), 7.32 (dd, 2H), 1.41 (s, 9H).
80% With tripotassium phosphate tribasic; copper (I) iodide; rac-diaminocyclohexane In 1,4-dioxane at 85℃; for 1.5h; Inert atmosphere; Intermediate 15-1 To a solution of 26.4 g (78.0 mmol) of Intermediate 7-1 in 250 mL of 1,4-dioxane was added 15.35 g (65.0 mmol) of 3,6-dichloro-9H-carbazole, 41.4 g (195.0 mmol) of potassium phos phate, 1.55 g (8.13 mmol) of copper iodide, 2.73 mL (22.75 mmol) of cyclohexane-1 ,2-diamine. The suspension was degassed with Ar, then heated to 85°C for 1.5 hours. After cooling to room temperature, the suspension was filtered over celite, rinsing with warm toluene (4x100 mL). The filtrate was evaporated, and the resulting residue was purified by silica-gel column chromatog raphy using heptanes as eluent. The resulting white solid was further recrystallized from cyclo hexane (2x150 mL) to give 14.66 g (80% yield) of Intermediate 15-1 as a white solid. 1H NMR (300 MHz, chloroform-o d 8.05 (dd, 2H), 7.67 (t, 1H), 7.50 (dt, 2H), 7.42 (dd, 2H), 7.32 (dd, 2H), 1.41 (s, 9H).
  • 49
  • [ 1510810-80-6 ]
  • [ 186772-43-0 ]
  • C30H36BrN [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With tetrakis-(triphenylphosphine)-palladium; sodium hydroxide In tetrahydrofuran; lithium hydroxide monohydrate for 1.5h; Inert atmosphere; Reflux; Intermediate 24-1 4.07 g (12.0 mmol) of Intermediate 7-1, 4.13 g (10.2 mmol) of Intermediate 2-3, 0.96 g (24.0 mmol) of sodium hydroxide were suspended in a mixture of tetrahydrofuran/water (54/27 ml_). The suspension was degassed with Ar, and 277 mg (2mol%) of tetrakis(triphenylphosphine)pal- ladium(O) were added to the reaction mixture. The reaction mixture was refluxed for 1.5 hours. The reaction was cooled to room temperature and diluted with toluene/water. The layers were separated, and the water layer was further extracted with toluene. The organic extracts were washed with water, brine and dried over sodium sulfate, filtered and evaporated. The residue was purified by silica-gel column chromatography using heptanes/toluene as eluent to give 4.30 g (73%yield) of Intermediate 24-1 as a white foam. ESI-MS:490.2 [M-H]-
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