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CAS No. : | 50548-45-3 | MDL No. : | MFCD00094238 |
Formula : | C12H7BrO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WUYYVOWEBMOELQ-UHFFFAOYSA-N |
M.W : | 247.09 | Pubchem ID : | 190542 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 13 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 61.42 |
TPSA : | 13.14 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.56 cm/s |
Log Po/w (iLOGP) : | 2.66 |
Log Po/w (XLOGP3) : | 4.57 |
Log Po/w (WLOGP) : | 4.35 |
Log Po/w (MLOGP) : | 3.5 |
Log Po/w (SILICOS-IT) : | 4.12 |
Consensus Log Po/w : | 3.84 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.94 |
Solubility : | 0.00285 mg/ml ; 0.0000115 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.57 |
Solubility : | 0.00666 mg/ml ; 0.000027 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.82 |
Solubility : | 0.000374 mg/ml ; 0.00000151 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.72 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
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 |
---|---|---|
100% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 24h;Reflux; | 31.3 g (126.7 mM) of <strong>[50548-45-3]1-bromodibenzo[b,d]furan</strong>, (<strong>[50548-45-3]1-bromodibenzo[b,d]furan</strong>),190.0 g (190.0 mM) bis (pinacolato) diboron, 4.6 g (6.3 mM) PdCl2(dppf) 37.3 g (380.1 mM) of KOAc was dissolved in 300 mL of 1,4-dioxane and refluxed for 24 hours. After the reaction was completed, distilled water and DCM (dichloromethane) were added at room temperature. The organic layer was dried with MgSO 4 and the solvent was removed by a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain the desired compound 1-5-3 37 g (quant.). |
98% | With palladium diacetate; calcium acetate; In N,N-dimethyl-formamide; at 80℃;Inert atmosphere; | 101g (410 mmol) of <strong>[50548-45-3]1-bromodibenzofuran</strong> was added to 500 ml flask under protectivegas, 273 g (1055 mmol) of bis (pinacolato) diborane (CAS 73183-34-3) wasdissolved in in 1500 ml dry DMF and degassed for 30 minutes. 121 g (1229 mmol) Calciumacetate and 8.4 g (37 mmol) palladium acetate are added subsequently, and thebatch was heated overnight at 80C . When the reaction was complete, themixture was diluted with 300 ml of toluene, and extracted with water. Thesolvent was removed in rotary evaporator, and the product was thenrecrystallized from heptane. Yield: 118 g (401mmol), 98% theory. |
70% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 10h;Reflux; | 500ml round bottom flask reactor, <strong>[50548-45-3]1-bromodibenzofuran</strong>(20.0g, 0.081mmol), bis(pinacolato)diboron (26.7g, 0.105mol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (1.3g, 0.002mol), potassium acetate (19.9g, 0.202mol), into a 1,4-dioxane 200ml were stirred for 10 hours under reflux after completion of the reaction was filtered a pad of celite. Filtrate was concentrated under a reduced pressure was separated and then the column was recrystallized from dichloromethane and heptane to give a intermediate 4-a> (17.0g, 70%). |
70% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 10h;Reflux; | 500ml round bottom flask reactor1-Bromo-dibenzofuran (20.0g, 0.081mmol), Bis (pinacolato) diboron (26.7g, 0.105mol),[1,1'-bis (diphenylphosphino) ferrocene] palladium in a Dijk (1.3g, 0.002mol),Potassium acetate (19.9g,0.202mol), into a 1,4-dioxane 200ml were stirred for 10 hours under reflux. After the completion of the reaction was filtered a pad of Celite. femaleAfter concentration under reduced pressure they were separated by liquid column and recrystallized with dichloromethane-heptane to give a (17.0g, 70%). |
70% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 10h;Reflux; | <strong>[50548-45-3]1-bromodibenzofuran</strong> (20.0 g, 0.081 mmol) was charged in a 500 ml round bottom flask reactor,Bis (pinacol) diboron (26.7 g, 0.105 mol)[1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (1.3 g, 0.002 mol)Potassium acetate (19.9 g, 0.202 mol), 200 ml of 1,4-dioxane and stirred under reflux for 10 hours.After the reaction was complete, the diatomaceous earth liner was filtered. The filtrate was concentrated under reduced pressure and then separated by column,And recrystallized from dichloromethane and heptane to obtain (17.0 g, 70%). |
70% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 1h;Reflux; | In a 500-mL round-bottom flask reactor, <strong>[50548-45-3]1-bromodibenzofuran</strong> (20.0 g, 0.081 mmol), bis(pinacolato)diboron (26.7 g, 0.105 mol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium (1.3 g, 0.002 mol), potassium acetate (19.9 g, 0.202 mol), and 1,4-dioxane (200 ml) were stirred together for hrs under reflux. After completion of the reaction, filtration was performed through a celite pad. The filtrate was concentrated in a vacuum, purified by column chromatography, and recrystallized in dichloromethane and heptane to afford <Intermediate 4-a> (17.0 g, 70%). |
70% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; for 10h;Reflux; | In a 500-mL round-bottom flask reactor, <strong>[50548-45-3]1-bromodibenzofuran</strong> (20.0 g, 81 mmol), bis(pinacolato)diboron (26.7 g, 105 mmol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium (1.3 g, 0.002 mol), potassium acetate (19.9 g, 202 mmol), and 1,4-dioxane (200 ml) were stirred together for 10 hrs under reflux. Concentration in a vacuum was followed by column chromatographic purification. Recrystallization in dichloromethane and heptane afforded (17.0 g, 70%). |
70% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 10h;Reflux; | Intermediate 8-a was synthesized according to Scheme 60 below:<strong>[50548-45-3]1-bromodibenzofuran</strong> (20.0g, 0.081mmol), bis (pinacolato) diboron (26.7g, 0.105mol) in 500ml round bottom flask reactor,200 ml of [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (1.3 g, 0.002 mol), potassium acetate (19.9 g, 0.202 mol) and 1,4-dioxane were added and stirred under reflux for 10 hours. . After the reaction was completed, the celite pad was filtered. The filtrate was concentrated under reduced pressure and column separatedRecrystallization from dichloromethane and heptane gave |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Sub 1-4-1 (4.94, 20mmol) was dissolved in anhydrous ether, lowering the temperature of the reaction to -78 °C, and dropwise addition of n-BuLi (2.5M in hexane) (1.4g, 22mmol) slowly, and after the reaction was stirred for 30 minutes. After lowering the temperature of the reaction back to -78 °C and dropwise added triisopropylborate (5.6g, 30mmol). Stirring at room temperature, diluted with water and it binds the 2N HCl. After the reaction was completed, the organic layer was dried and extracted with water and ethyl acetate with MgSO4 and concentrated and to the resulting organics silicagel column and recrystallized to obtain 3.14g of Sub 1(33) (yield: 74percent). | |
72.8% | Into a 1 L four-necked round bottom flask equipped with a stirrer, a Liebig condenser fitted with a calcium chloride tube, a nitrogen inlet tube, a 200 mL isobaric dropping funnel and a thermometer, 34.5 g of the bromide obtained in the above (139.6 mmol) of dehydrated THF and 325 mL of dehydrated THF, and the mixture was cooled to -60 ° C. or lower in an acetone-dry ice bath under a nitrogen stream. Subsequently, 106 mL (167.6 mmol) of n-BuLi was added dropwise at -50 ° C. or lower, then the isobaric dropping funnel was washed with 100 mL of THF and added to the reaction solution. Subsequently, after postreaction at -50 ° C. or lower for 1 hour, 43 mL (181.6 mmol) of [B (i-PrO) 3] was added dropwise at -45 ° C. or lower. Subsequently, the isobaric dropping funnel was washed with 80 mL of THF and added to the reaction solution, followed by stirring at -45 ° C. or lower for 30 minutes. The acetone-dry ice bath was removed, the temperature was returned to room temperature, and the reaction was continued for additional 20 hours to obtain boron To obtain a reaction solution.Next, 24 mL of concentrated hydrochloric acid and 241 mL of water were placed in a 1 L four-necked round bottom flask equipped with a stirring device, a Liebig condenser (not required), a 1 L dropping funnel and a thermometer, ° C. Subsequently, the boron reaction solution was dropped at a temperature not exceeding 10 ° C., and the mixture was stirred at 10 ° C. or less for 1 hour, then returned to room temperature and stirred for 3 hours.The obtained reaction solution was transferred to a 1 L separating funnel, the organic layer was separated, and the aqueous layer was extracted with 340 mL of ethyl acetate. Next, the organic layers were combined and washed with saturated brine 240 mL, dried over magnesium sulfate, magnesium sulfate was removed by suction filtration, and the solvent was distilled off under reduced pressure. Subsequently, 220 mL of n-heptane was added to the obtained crude crystals, rinsed at 50 ° C. for 1 hour, cooled to room temperature and filtered by suction to obtain 21.6 g of the desired boronic acid (yield 72.8percent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.5% | With sodium hydride; In water; N,N-dimethyl-formamide; paraffin oil; at 5 - 100℃; for 1.08333h; | 111 g (416mmol) of 6'-bromo-2'-fluorobiphenyl-2-ol was dissolved in 2 ? of SeccoSolv DMF (up to 0.003% H2O), and cooled to 5C . 20 g (449 mmol) of sodium hydride (60% suspension in paraffin oil) was added to the solution (in portions) wasadded gradually to the solution and the mixture is stirred for 20 min. Aftercompletion of the addition, the mixture was heated for 45 min at 100 . After cooling, 500 ml ethanol wasadded slowly to a mixture, then ethanol was evaporated in a rotary evaporatorand then purified by chromatography. Yield : 90 g (367 mmol), theory 88.5%. |
88.5% | With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 5 - 100℃; for 1.08333h; | 111 g (416 mmol) of 6?-bromo-2?-fluorobiphenyl-2-ol are dissolved in 21 of SeccoSolv DMF (max 0.003% of H20) and cooled to 5C. 20 g (449 mmol) of sodium hydride (60% suspension in paraffin oil) are added in portions tothis solution, and the mixture is stirred for a further 20 mm. after the addition is complete and then heated at 100C for 45 mm. After cooling, 500 ml of ethanol are slowly added to the mixture, which is then evaporated to dryness in a rotary evaporator and purified by chromatography. Yield: 90 g (367 mmol), 88.5% of theory. |
88.5% | With sodium hydride; In N,N-dimethyl-formamide; paraffin oil; at 5 - 100℃; for 1.08333h; | 111 g (416 mmol) 6'-bromo-2'-fluoro-biphenyl-2-ol are dissolved in 2 L DMF (max 0.003% H2O) SeccoSolv and cooled to 5 0 C. 20 g (449 mmol) of sodium hydride (60% suspension in paraffin oil) are added to this solution portion by portion. The mixture is stirred 20 min and then heated to 100 0 C during 45 min. The mixture is slowly mixed after cooling with 500 ml of ethanol, and then evaporated and purified by chromatography. (0147) Yield: 90g (367 mmol), 88.5% of theory. |
88.5% | With sodium hydride; In water; N,N-dimethyl-formamide; paraffin oil; at 5 - 100℃; for 1.08333h;Inert atmosphere; | 111 g (416 mmol) of 6-bromo-2?-fluorobiphenyl-2-ol are dissolved in 2 1 of DMF (max. 0.003% H20) SeccoSolv and cooled to 5 C. 20 g (449 mmol) of sodium hydride (60% suspension in paraffin oil) are added to this solution in portions, once the addition has ended the mixture is stirred for 20 mm, and then the mixture is heated to 1000 C. for 45 mm. After cooling, 500 ml of ethanol are added gradually to the mixture, which is concentrated by rotary evaporation and purified by chromatography. Yield: 90 g (367 mmol), 88.5% of theory. |
88.5% | With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 5 - 100℃; for 1.08333h; | 111 g (416 mmol) of 6?-bromo-2?-fluorobiphenyl-2-ol are dissolved in 2 l of DMF (max. 0.003% H2O) SeccoSolv and cooled to 5 C. 20 g (449 mmol) of sodium hydride (60% suspension in paraffin oil) are added to this solution in portions, once the addition has ended the mixture is stirred for 20 min, and then the mixture is heated to 100 C. for 45 min. After cooling, 500 ml of ethanol are added gradually to the mixture, which is concentrated by rotary evaporation and then purified by chromatography. Yield: 90 g (367 mmol), 88.5% of theory. |
85% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 2h;Large scale; | To a 50 L reactor was added 2.51 Kg (9.4 mol) of 2'-bromo-6'-fluorobiphenyl-2-ol, 15 L of N,N-dimethylformamide, and 2.59 Kg (18.8 mol) of potassium carbonate, the temperature was raised to 100 degrees, reaction 2h, The heating was stopped, the reaction was completed, and after the reaction system was cooled to room temperature, 25 L of water, 12 L of o-dichloroethane was added to the reaction mixture, and the mixture was stirred for 5 minutes. After standing, the liquid phase was taken, and the organic phase was obtained, and then washed twice with 5 L of water, and the mixture was separated and dried with 400 g of anhydrous sodium sulfate for 2 hours. After suction filtration, the o-dichloroethane was spin-dried under reduced pressure at 50 C, dissolved in 4 L of petroleum ether (silica gel 2.5 Kg), rinsed with petroleum ether, the unknown impurities were removed, and spin-dried to obtain 1-bromodibenzofuran 1.97 Kg, White solid, purity 99.8%, yield 85%. |
8.55% | With sodium hydride; In water; N,N-dimethyl-formamide; paraffin oil; at 5 - 100℃; for 1.08333h; | 111 g (416 mmol) of 6'-bromo-2'-fluorobiphenyl-2-ol was dissolved and cooled to 5 C in 2 L of DMF (up to 0.003% H2O) SeccoSolv. To this solution was added 20 g (449 mmol) of sodium hydride (60% paraffin oil suspension) in portions and the mixture was stirred for 20 minutes once the addition was complete,The mixture was then heated to 100 C for 45 minutes. After cooling, 500 ml of ethanol was gradually added to the mixture,Concentration by rotary evaporation followed by purification by chromatography. Yield: 90 g (367 mmol), theoretical 8.55%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sulfuric acid; iodine; acetic acid; periodic acid; In chloroform; water; at 65℃; for 3h; | 20 g (80 mmol) of dibenzofuran-1-boronic acid, 2.06 g(40.1 mmol) of iodine, 3.13 g (17.8 mmol) of periodic acid, 80 ml of aceticacid, 5 ml of sulfuric acid, 5 ml water and 2 ml chloroform were stirred at 65C for 3 h. After cooling, water was added to the mixture, and the precipitatedsolids were filtered off with suction, and washed three times with water. Thenthe product was recrystallized from dichloromethane / heptane. The yield is25.6 g (68 mmol), equivalent to 85% of theory. |
85% | With sulfuric acid; iodine; iodic acid; acetic acid; In chloroform; water; at 65℃; for 3h; | 20 g (80 mmol) of dibenzofuran-1-boronic acid, 2,06 g (40,1 mmol) of iodine, 3.13 g (17,8 mmol) of iodic acid, 80 ml of acetic acid, 5 ml of sulfuric acid, 5 ml of water and 2 ml of chloroform are stirred at 65 during 3 hours. After cooling, the mixture is mixed with water, the precipitated solid is removed, and the residue is washed three times with water. The residue is recrystallized from toluene and dichloromethane/heptane. (0151) The yield is 25.6 g (68 mmol), corresponding to 85% of theory. |
85% | With sulfuric acid; iodine; iodic acid; acetic acid; In chloroform; water; at 65℃; for 3h; | 20 g (80 mmol) of <strong>[50548-45-3]1-bromodibenzofuran</strong>, 2.06 g (40.1 mmol) of iodine,3.13 g (17.8 mmol) of iodic acid,80ml acetic acid and 5ml sulfuric acid and5ml water and2 ml of chloroform were stirred at 65 C for 3 hours.After cooling, the mixture is mixed with water,The precipitated solid was filtered off with suction and washed three times with water. The residue is recrystallized from toluene and with methylene chloride / heptane. The yield was 25.6 g (68 mmol), corresponding to a theoretical yield of 85%. |
85% | With sulfuric acid; iodine; iodic acid; acetic acid; In chloroform; water; at 65℃; for 3h;Inert atmosphere; | 20 g (80 mmol) of dibenzofuran-l-boronic acid, 2.06 g (40.1 mmol) of iodine, 3.13 g (17.8 mmol) of iodic acid, 80 ml of acetic acid, 5 ml of sulphuric acid, 5 ml of water and 2 ml of chloroform are stirred at 65 C. for 3 h. After cooling, the mixture is admixed with water, and the precipitated solids are filtered off with suction and washed three times with water. The residue is recrystallized from toluene and from dichloromethane/heptane. The yield is 25.6 g (68 mmol), corresponding to 85% of theory. |
85% | With sulfuric acid; iodine; iodic acid; acetic acid; In chloroform; water; at 65℃; for 3h; | 20 g (80 mmol) of <strong>[50548-45-3]1-bromodibenzofuran</strong>, 2.06 g (40.1 mmol) of iodine, 3.13 g (17.8 mmol) of iodic acid, 80 ml of acetic acid and 5 ml of sulphuric acid and 5 ml of water and 2 ml of chloroform are stirred at 65 C. for 3 h. After cooling, the mixture is admixed with water, and the precipitated solids are filtered off with suction and washed three times with water. The residue is recrystallized from toluene and from dichloromethane/ heptane. The yield is 25.6 g (68 mmol), corresponding to 85% of theory. |
83% | With sulfuric acid; iodine; iodic acid; acetic acid; at 65℃; for 3h; | Compound B-3 (40 g, 161.9 mmol) was dissolved in acetic acid (200 mL).To this was added iodine (4.16 g, 81.0 mmol),Iodic acid (6.3 g, 36.0 mmol),And sulfuric acid (10 mL), and the mixture was stirred at 65 C for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature,Water was added.The resulting solid was filtered, washed with water and then recrystallized from toluene and ethyl acetate to obtain Compound B-4 (50.1 g, yield 83%). |
83% | With sulfuric acid; iodine; iodic acid; acetic acid; at 65℃; for 3h; | Compound B-3 (40 g, 161.9 mmol) was dissolved in acetic acid (200 mL). To this was added iodine (4.16 g, 81.0 mmol), iodic acid (6.3 g, 36.0 mmol), and sulfuric acid (10 mL) and the mixture was stirred at 65 C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature and water was added thereto. The resulting solid was filtered, washed with water and then recrystallized with toluene and ethyl acetate to obtain 50.1 g (yield: 83%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | 180g (728 mmol) of <strong>[50548-45-3]1-bromodibenzofuran</strong> was dissolved in 1500 ml dry THF, and cooledto -78.At this temperature, 305 ml (765 mmol/2.5M hexane) of n-butyl lithium was addedfor about 5 min. The mixture was subsequently stirred at -78 C for 2.5 h. Atthis temperature, 151 g (1456 mmol) trimethylborate was added rapidly and leavethe reaction (about 18 h) slowly to room temperature. The reaction solution waswashed with water, precipitated solids were filtered, and the organic phase wasthen azeotropically distilled with toluene. The crude product was washed bystirring with toluene/dichloromethane at about 40 C, and filtered with suction.Yield: 146 g (690 mmol), theoretical 95percent. | |
95% | 180 g (728 mmol) of <strong>[50548-45-3]1-bromodibenzofuran</strong> are dissolved in 1500 ml of dry THF and cooled to -78°C. 305 ml (764 mmol I 2.5 M in hexane) of n-butyllithium are added over the course of about 5 mm. at this temperature, and the mixture is subsequently stirred at -78°C for a further 2.5 h. 151 g (1456 mmol) of trimethyl borate are added as rapidly as possible at this temperature, and the reaction is slowly allowed to come to room temperature(about 18 h). The reaction solution is washed with water, and the solid which has precipitated out and the organic phase are dried azeotropically with toluene. The crude product is washed by stirring with toluene/methylene chloride at about 40°C and filtered off with suction. Yield: 146 g (690 mmol),95percent of theory. | |
95% | 180 g (728 mmol) of <strong>[50548-45-3]1-bromo-dibenzofuran</strong> are dissolved in 1500 ml_ of dried THF and cooled to -78° C. At this temperature, 305 ml_ (764 mmol / 2.5 M in hexane) of n-butyl lithium is added within about 5 min to the mixture, which is then stirred during 2,5 hours at -78 ° C. At this (0155) temperature, 151 g (1456 mmol) of trimethyl borate is added as quickly as possible to the mixture and the reaction mixture is allowed to slowly warm to room temperature (about 18h). The reaction solution is washed with water and the precipitated solid and the organic phase are dried with toluene. The crude product is extracted out of toluene/methylene chloride at about 40° C. Yield: 146 g (690 mmol), 95percent of theory. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
equipped with a pressure-equalizing dropping funnel 2L three-necked flask, metal magnesium (5.1g, 0.21mol), <strong>[50548-45-3]1-bromo-dibenzofuran</strong> (49.1g, 0.2mol) was dissolved in 450g of tetrahydrofuran, and placed in a constant pressure funnel, a nitrogen, three bottles heated to an inner temperature reaches 65 , through a pressure-equalizing dropping funnel was added <strong>[50548-45-3]1-bromo-dibenzofuran</strong> tetrahydrofuran, was added 1-bromo-time first one fifth of tetrahydrofuran dibenzofuran, after the initiation of the reaction, the remaining portion was slowly added dropwise, for 1.5 h addition was complete, the reaction at the reflux temperature IH, stand.2-bromo-fluorenone (51.8g, 0.2mol) was dissolved in 220g of tetrahydrofuran, and then slowly poured into the above three bottles, the reflux temperature of the reaction 3h, after the completion of the reaction, was cooled to 25 , the above reaction solution was slowly the mass was poured into 200g of 10percent concentration diluted hydrochloric acid, stirred for 15min, liquid separation, the organic phase was collected, the solvent removed under reduced pressure to give a crude product of compound 1, 82.1 g viscous liquid, the crude product of the above compound no purified, was used directly in the next reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 10h;Reflux; | In a 500 ml round bottom flask reactor 1-Bromodibenzofuran (1.3g, 0.002mol) of bis (pinacolato) diboron (26.7g, 0.105mol), [1,1'-bis (diphenylphosphino) ferrocene] dichloro palladium (20.0g, 0.081mmol) , Potassium acetate (19.9 g, 0.202 mol) and 1,4-dioxane (200 ml) were added and the mixture was stirred under reflux for 10 hours. After completion of the reaction, the celite pad was filtered. The filtrate was concentrated under reduced pressure, the column was separated, and recrystallized from dichloromethane and heptane to obtain (17.0 g, 70percent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 100℃; for 12h; | A 2 L reactor was charged with [Intermediate 1-a] (52 g, 177 mmol) 2-Biphenylboronic acid (42 g, 212 mmol),Tetrakis (triphenylphosphine) palladium (4.1 g, 3.5 mmol),Potassium carbonate (73.4 g, 531 mmol), toluene (600 mL) and distilled water (200 mL) were added, and the mixture was stirred at 100 ° C for 12 hours.After cooling to room temperature, the organic layer was extracted with ethyl acetate.The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain [intermediate 1-b]. (41 g, 72percent). <strong>[50548-45-3]1-bromodibenzofuran</strong> was used instead of [Intermediate 1-a] used in the above Synthesis Example 1- (2) Was synthesized in the same manner as in [Intermediate 4-a]. (57 g, 68percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; for 6h;Inert atmosphere; Reflux; | To a 500 ml round bottom flask in a nitrogen atmosphereCompound 1-Bromobenzofuran (10.0 g, 40.65 mmol),N - ([1,1'-biphenyl] -4-yl) - [1,1 ': 4', 1 '' - terphenyl]-4-amine ((N - ([1,1'-biphenyl] -4-yl) - [1,1 ': 4', 1 '' - terphenyl]-4-amine)(17.75 g, 44.72 mmol)Xylene(Xylene)After completely dissolved Sodium tert-butoxide(sodium tert-butoxide)(5.08 g, 52.85 mol) was added,Bis (tri-tert-butylphosphine) palladium (0)(Bis (tri-tert-butylphosphine) palladium (0)) (0.21 g, 0.41 mmol)And the mixture was heated and stirred for 6 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (250 ml) to obtain Compound (4) (18.89 g, yield: 82%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; for 3h;Inert atmosphere; Reflux; | To a 500 ml round bottom flask in a nitrogen atmosphereCompound 1-Bromobenzofuran (10.0 g, 40.65 mmol),N- (4- (triphenylene-2-yl) phenyl) - [1,1'-biphenyl] -4- amine(N- (4- (triphenylen-2-yl) phenyl) - [1,1'-biphenyl] -4-amine)(17.75 g, 44.72 mmol)Xylene(Xylene) in 320 mlAfter complete dissolution, sodium tert-butoxide(sodium tert-butoxide) (5.08 g, 52.85 mol), And bis (tri-tert-butylphosphine) palladium (0)(Bis (tri-tert-butylphosphine) palladium (0))(0.21 g, 0.41 mmol), and the mixture was heated with stirring for 3 hours. After the temperature was lowered to room temperature, the salt was removed by filtrationXylene was concentrated under reduced pressure and recrystallized from 180 ml of tetrahydrofuran to obtain the above compound 5 (17.75 g, yield:68percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; for 3h;Inert atmosphere; Reflux; | To a 500 ml round bottom flask in a nitrogen atmosphereCompound 1-Bromobenzofuran (10.0 g, 40.65 mmol),Di ([1,1'-biphenyl] -4-yl) amine(di ([1,1'-biphenyl] -4-yl) amine) (18.38 g, 44.72 mmol)Xylene(Xylene) in 310 mlAfter complete dissolution, sodium tert-butoxide (sodium tert-butoxide) (5.08 g, 52.85 mol) Bis (tri-tert-butylphosphine) palladium (0)(Bis (tri-tert-butylphosphine) palladium (0)) (0.21 g, 0.41 mmol)And the mixture was heated and stirred for 3 hours.After the temperature was lowered to room temperature and the salts were removed by filtration, xylene was concentrated under reduced pressure and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 15 to prepare Compound 6 (12.84 g, yield 65percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; for 6h;Inert atmosphere; Reflux; | To a 500 ml round bottom flask in a nitrogen atmosphereCompound 1-Bromobenzofuran (10.0 g, 40.65 mmol),N-phenyl- [1,1 ': 4', 1 ": 4", 1 "'-tetraphenyl] (N-phenyl- [1,1 ': 4', 1 ": 4", 1 "-quaterphenyl] -4-amine (17.75 g, 44.72 mmol) Xylene(Xylene) dissolved in 330 ml Sodium tert-butoxide(sodium tert-butoxide) (5.08 g, 52.85 mol), And bis (tri-tert-butylphosphine) palladium (0)(Bis (tri-tert-butylphosphine) palladium (0)) (0.21 g, 0.41 mmol)And the mixture was heated and stirred for 6 hours.After the temperature was lowered to room temperature and the salt was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250 ml of ethyl acetate to obtain Compound 7 (18.89 g, yield: 82percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; for 3h;Inert atmosphere; Reflux; | To a 500 ml round bottom flask in a nitrogen atmosphereCompound 1-Bromobenzofuran (10.0 g, 40.65 mmol), Di ([1,1'-biphenyl] -4-yl) amine (14.35 g, 44.72 mmol)Was completely dissolved in 240 ml of xylene and then sodium tertbutoxide(sodium tertbutoxide) (5.08 g, 52.85 mol) was added,Bis (tri-tert-butylphosphine) palladium (0)(Bis(tri-tert-butylphosphine)palladium(0)) (0.21 g, 0.41 mmol) was added thereto and the mixture was heated with stirring for 3 hours.After the temperature was lowered to room temperature and the salts were removed by filtration, xylene was concentrated under reduced pressure and the residue was subjected to column chromatography using tetrahydrofuran: hexane = 1: 15 to prepare Compound 1 (12.84 g, yield 65percent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; for 5h;Inert atmosphere; Reflux; | To a 500 ml round bottom flask in a nitrogen atmosphereCompound 1-Bromobenzofuran (10.0 g, 40.65 mmol),Di ([1,1'-biphenyl] -4-yl) amine(di ([1,1'-biphenyl] -4-yl) amine) (14.35 g, 44.72 mmol)Xylene(Xylene) After dissolving, sodium tert-butoxide(sodium tert-butoxide) (5.08 g, 52.85 mol), And bis (tri-tert-butylphosphine) palladium (0)(Bis (tri-tert-butylphosphine) palladium (0)) (0.21 g, 0.41 mmol) was added and the mixture was heated with stirring for 5 hours.After lowering the temperature to room temperature and removing the salt by filtration, the xylene was concentrated under reduced pressure, and tetrahydrofuran: hexAcid = 1: 25, to obtain Compound 2 (10.47 g, yield: 53percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; for 7h;Inert atmosphere; Reflux; | To a 500 ml round bottom flask in a nitrogen atmosphereCompound 1-Bromobenzofuran (10.0 g, 40.65 mmol),1,1'-biphenyl] -4-yl) - [1,1 ': 3', 1 '' - terphenyl(N - ([1,1'-biphenyl] -4-yl) - [1,1 ': 3', 1 '' - terphenyl]"(17.75 g, 44.72 mmol) Xylene(Xylene) in 260 mlAfter completely dissolvedSodium tert-butoxide(sodium tertbutoxide) (5.08 g, 52.85 mol) was added,Bis (tri-tert-butylphosphine) palladium (0)(Bis (tri-tert-butylphosphine) palladium (0)) (0.21 g, 0.41 mmol)And the mixture was heated and stirred for 7 hours.The temperature was lowered to room temperature and filteredAfter the salt was removed, xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (200 ml) to obtain Compound (3) (16.17 g, yield: 71percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | All experimental instruments were fully dried beforehand. 26.3 g 1-bromobiphenylfuran was placed into a three-neck flask (2 L), to which 500 mL dry tetrahydrofuran was added to dissolve the solid. Then the resulting mixture was cooled down to ?78° C. and 52.5 mL LDA solution (1.05 eq., 2M) in THF was added dropwise. After the addition the resulting mixture was stirred at the above temperature for 1 hour and 28.0 g iodine (1.1 eq.) was added dropwise. After the addition the resulting mixture was stirred overnight at room temperature. After the reaction finished, hydrochloric acid solution (4M) was added and the resulting mixture was extracted with dichloromethane. The organic phase was washed with saturated aqueous NaCl solution until neutral and dried. The solvent was then removed by rotary evaporation and the residual was recrystallized with toluene and ethanol to produce 38.5 g Intermediate h in 79percent yield | |
79% | The experimental apparatus was thoroughly dried and 26.3 g of <strong>[50548-45-3]1-bromodibenzofuran</strong> was added to a 2L three-necked flask.After adding 500 mL of dried tetrahydrofuran, the solution was cooled down to ?78° C., and 52.5 mL of a 2 M solution of LDA (1.05 eq.) in THF was added dropwise. End of drippingAfter stirring at this temperature for 1 hour, 28.0 g of iodine (1.1 eq.) was added at this temperature. After the addition was completed, the mixture was stirred at room temperature overnight.After the reaction is completed, 4M hydrochloric acid solution is added and extracted with dichloromethane. The organic phase is washed with saturated brine until neutral, dried and removed.The solvent was recrystallized from toluene and ethanol to obtain 38.5 g of the intermediate h in a yield of 79percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; for 13h;Reflux; | 2.3 g (24.7 mmol) of aniline, 7.4 g (30 mmol) of <strong>[50548-45-3]1-bromodibenzofuran</strong>, 0.4 g (0.3 mmol) of palladium acetate, 4.2 g (43 mmol) of sodium tertiary butoxide, 0.1 g (0.3 mmol) of tri-tert-butylphosphine, 100 ml of toluene was added and the mixture was refluxed and stirred for 13 hours. After completion of the reaction, the reaction mixture was filtered, and the filtrate was concentrated and separated by column chromatography to obtain 4.0 g of Intermediate 7-a. (Yield: 63percent). |
63% | With palladium diacetate; triphenylphosphine; sodium t-butanolate; In toluene; for 13h;Reflux; | A 250 ml reactor was charged with 2.3 g (24.7 mmol) of aniline, 7.4 g (30 mmol) of <strong>[50548-45-3]1-bromodibenzofuran</strong>, 0.4 g (0.3 mmol) of palladium acetate,4.2 g (43 mmol) of sodium tertiary butoxide, 0.1 g (0.3 mmol) of tri-tert-butylphosphine,100 ml of toluene was added and the mixture was refluxed and stirred for 13 hours.After completion of the reaction, the reaction mixture was filtered, and the filtrate was concentrated and separated by column chromatography to obtain 4.0 g of Intermediate 8-a. (Yield: 63percent) |
Tags: 50548-45-3 synthesis path| 50548-45-3 SDS| 50548-45-3 COA| 50548-45-3 purity| 50548-45-3 application| 50548-45-3 NMR| 50548-45-3 COA| 50548-45-3 structure
[ 955959-84-9 ]
4-(4-Bromophenyl)dibenzo[b,d]furan
Similarity: 0.92
[ 955959-84-9 ]
4-(4-Bromophenyl)dibenzo[b,d]furan
Similarity: 0.92
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