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[ CAS No. 955959-84-9 ] {[proInfo.proName]}

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Chemical Structure| 955959-84-9
Chemical Structure| 955959-84-9
Structure of 955959-84-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 955959-84-9 ]

CAS No. :955959-84-9 MDL No. :MFCD19441306
Formula : C18H11BrO Boiling Point : -
Linear Structure Formula :- InChI Key :RIPZSADLUWTEFQ-UHFFFAOYSA-N
M.W : 323.18 Pubchem ID :59022098
Synonyms :

Calculated chemistry of [ 955959-84-9 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 19
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 86.86
TPSA : 13.14 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.41
Log Po/w (XLOGP3) : 5.98
Log Po/w (WLOGP) : 6.02
Log Po/w (MLOGP) : 4.74
Log Po/w (SILICOS-IT) : 5.65
Consensus Log Po/w : 5.16

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.25
Solubility : 0.000183 mg/ml ; 0.000000565 mol/l
Class : Poorly soluble
Log S (Ali) : -6.03
Solubility : 0.0003 mg/ml ; 0.000000928 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.31
Solubility : 0.00000159 mg/ml ; 0.0000000049 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.73

Safety of [ 955959-84-9 ]

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:

Application In Synthesis of [ 955959-84-9 ]

* 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.

  • Upstream synthesis route of [ 955959-84-9 ]
  • Downstream synthetic route of [ 955959-84-9 ]

[ 955959-84-9 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 100124-06-9 ]
  • [ 589-87-7 ]
  • [ 955959-84-9 ]
YieldReaction ConditionsOperation in experiment
93% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 8 h; Inert atmosphere In a nitrogen atmosphere, dibenzofuran-4-ylboronic acid (100 g, 472 mmol) was dissolved in 1,000 mL of tetrahydrofuran (THF)1-bromo-4-iodobenzene (160 g, 556 mmol) and tetrakis (triphenylphosphine) palladium (5.45 g, 4.72 mmol) were added thereto and stirred.Potassium carbonate (78.3 g, 566 mmol) saturated with water was added and the mixture was refluxed by heating at 80 ° C for 8 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM). Then, water was removed with anhydrous MgSO 4,Filtered and concentrated under reduced pressure.The thus-obtained residue was purified by flash column chromatography to obtain Compound I-9 (142 g, 93percent).
89% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12 h; Reflux; Inert atmosphere To a round bottom flask, 4-dibenzofuran boronic acid 20g (94.3mmol), 1- bromo-4-iodo benzene  26.7g (94.3mmol) was put and toluene (313ml) mmol) was added and dissolved and then an aqueous solution 117ml of potassium carbonate 19.5g (141.5 mmol)dissolved was added and stirred. Here, tetrakis triphenylphosphine palladium 1.09g (0.94mmol)was added and stirred under reflux for 12 hours under a nitrogen atmosphere.After the end of the reaction and the extract was extracted to ethyl acetate, the extract was dried and filtered through magnesium sulfate, and the filtrate was concentrated under reduced pressure.The product n- hexane / dichloromethane (9: 1 volumetric ratio) was purified by silica gel column chromatography to give the 27g (89percentyield) of the aimed compound intermediate M-1 as a white solid.
89% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12 h; Inert atmosphere; Reflux 4-dibenzofuran boronic acid 20g (94.3mmol) in a round bottom flask, 1-bromo-4-iodo benzene, 26.7g (94.3mmol) And stirred into 117ml aqueous solution was added to dissolve the potassium carbonate and 19.5g (141.5mmol) was dissolved was added to toluene (313ml). Followed by adding thereto tetrakis triphenylphosphine palladium 1.09g (0.94mmol) was stirred under reflux for 12 hours under a nitrogen atmosphere. After the end of the reaction the extract was concentrated to dryness and extracted with ethyl acetate and filtered through a magnesium sulfate, and the filtrate under reduced pressure. The product n- hexane / dichloromethane (9: 1 by volume) was purified by a silica gel column chromatography to give the intermediate M-1 as a white solid 27g (89percent yield).
89% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12 h; Reflux; Inert atmosphere 4-dibenzofuran boronic acid 20g (94.3mmol) and 1-bromo-4-iodo benzene 26.7g(94.3mmol) in toluene (313 ml) was added in a round bottom flask and stirred, an aqueous solution (117 ml) of potassium carbonate 19.5g (141.5mmol) was added, followed by adding tetrakistriphenylphosphine palladium 1.09g (0.94mmol) and stirred under reflux for 12 hours under a nitrogen atmosphere. After the end of the reaction, the reaction mixture was extracted with ethyl acetate, dried using magnesium sulfate, and the filtrate was concentrated under reduced pressure. The obtained product was purified by silica gel column chromatography using n-hexane/dichloromethane (9: 1 by volume) to give the desired intermediate compound M-1 27g (89percent yield) as a white solid.
89% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 12 h; Inert atmosphere; Reflux 4-benzofuran boronic acid (4-dibenzofuranboronic acid) 20g (94.4mmol), 1- bromo-4-iodo-benzene 28g (99.2mmol) and tetrakistriphenylphosphine palladium flask 1.08g (0.94mmol) put in was dissolved in 240ml of toluene and 120mL of ethanol under a nitrogen atmosphere after the addition of an aqueous solution of potassium carbonate dissolved in 120ml 28g (188.8mmol) it was stirred under reflux for 12 hours. After the reaction the extract was dried, filtered and then extracted with ethyl acetate and with magnesium sulfite and concentrated under reduced pressure of the filtrate. The product n- hexane / dichloromethane (9: 1 by volume) as the desired compound of intermediate M-9 was purified by silica gel column chromatography to give a 27g (89percent yield) as a white solid.
89% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12 h; Inert atmosphere; Reflux Will be 20 grams (94.3 millimoles) 4-dibenzofuran boric acid and 26.7 g (94.3 mmol) 1-Bromo-4-iodobenzene was placed in a round bottom flask, and 313 ml of toluene was added thereto to dissolve it. A 117 ml aqueous solution obtained by dissolving 19.5 g (141.5 mmol) of potassium carbonate was added thereto, and the mixture was agitated. Subsequently, 1.09 g (0.94 mmol) of tetratriphenylphosphine palladium was added thereto. The resulting mixture was refluxed under a nitrogen atmosphere and stirred for 12 hours. When the reaction was completed, the resultant was extracted with ethyl acetate. The extracted solution was dried over magnesium sulfate and filtered. The filtered solution was concentrated under reduced pressure. Subsequently, the product obtained therefrom was treated with n-hexane/dichloromethane (9:1 vol/vol) Purified by gel column chromatography, Obtained 27 g of intermediate M-1 as a white solid (yield: 89percent).
81% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene for 10 h; Inert atmosphere; Reflux [Production Example 1] Synthesis of 4-(4-bromophenyl)dibenzofuran Under an argon atmosphere, 300 mL of toluene and 150 mL of a 2-M aqueous solution of sodium carbonate were added to 28.3 g (100 mmol) of 4-iodobromobenzene, 22.3 g (105 mmol) of dibenzofuran-4-boronic acid, and 2.31 g (2.00 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was refluxed under heat for 10 hours. Immediately after the completion of the reaction, the resultant was filtrated, and then the water layer was removed. The organic layer was dried with sodium sulfate, and was then concentrated. The residue was purified by silica gel column chromatography, whereby 26.2 g of the white crystal of 4-(4-bromophenyl)dibenzofuran were obtained (81percent yield).
81% With sodium carbonate In water; toluene for 10 h; Reflux; Inert atmosphere <Synthesis Example 5 (Synthesis of Intermediate 5)>; Under the atmosphere of argon gas, 300 ml of toluene and 150 ml of 2 M concentration sodium carbonate aqueous solution was added to 28.3 g (100 mmol) of 4-iodobromobenzene, 22.3 g (105 mmol) of dibenzofurazi-4-boronic acid and 2.31 g (2. 00 mmol) of tetrakis(triphenylphosphine)palladium (0), and the resultant mixture solution was heated while refluxing for 10 hours. After the reaction was completed, filtration was carried out immediately and a water layer was removed. After drying the organic layer over sodium sulfate, the resultant was concentrated. The residue was subjected to a chromatography purification using a silica gel column to obtain 26.2 g of 4-(4-bromophenyl)dibenzofuriran in the state of a white crystal (yield:81percent). The resultant white crystal was identified as Intermediate 5 from the result in accordance with the FD-MS analysis.
81% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water; toluene for 10 h; Inert atmosphere; Reflux In an argon atmosphere, 150 ml of toluene, 150 ml of dimethoxyethane, and 150 ml (300.0 mmol) of a 2 M aqueous solution of Na2CO3 were added to a mixture of 28.3 g (100.0 mmol) of 4-iodobromobenzene, 22.3 g (105.0 mmol) of dibenzofuran-4-boronic acid and 2.31 g (2.00 mmol) of Pd[PPh3]4, and the resultant mixture was stirred for 10 h while refluxing under heating. [0160] After the reaction, the reaction product extracted with dichloromethane in a separatory funnel. The organic layer was dried over MgSO4, filtered, and then concentrated. The concentrate was purified by silica gel column chromatography, to obtain 26.2 g of a white solid, which was identified as the following intermediate 1-5 by FD-MS analysis (yield: 81percent).
81% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water; toluene for 10 h; Inert atmosphere; Reflux [0184] In an argon atmosphere, 28.3 g (100.0 mmol) of 4-iodobromobenzene, 22.3 g (105.0 mmol) of dibenzofuran-4-boronic acid and 2.31 g (2.00 mmol) of Pd[PPh3]4 were added with 150 ml of toluene, 150 ml of dimethoxyethane and150 ml (300.0 mmol) of a 2 M aqueous solution of Na2CO3. The resultant mixture was stirred for 10 h while refluxingunder heating.[0185] After the reaction, the mixture was extracted with dichloromethane in a separatory funnel. The organic layerwas dried over MgSO4, filtered, and then concentrated. The concentrate was purified by silica gel column chromatographyto obtain 26.2 g of white solid, which was identified as the following intermediate 1-4 by FD-MS (yield: 81percent)
81% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water; toluene for 10 h; Inert atmosphere; Reflux INTERMEDIATE SYNTHESIS 1-1 (Synthesis of intermediate 1-1) [0106] Under an argon atmosphere, into a mixture of 28.3 g (100.0 mmol) of 4-iodobromobenzene, 22.3 g (105.0 mmol) of dibenzofuran-4-boronic acid, and 2.31 g (2.00 mmol) of Pd[PPh3]4, 150 ml of toluene, 150 ml of dimethoxyethane, and 150 ml (300.0 mmol) of a 2 M aqueous solution of Na2CO3 were added, and the resultant mixture was stirred for 10 h while refluxing under heating. [0107] After the reaction, the obtained mixture was cooled to room temperature and extracted with dichloromethane in a separatory funnel. The organic layer was dried over MgSO4, and then filtered and condensed. The condensate was purified by silica gel column chromatography to obtain 26.2 g of a white solid, which was identified as the intermediate 1-1 by FD-MS analysis (Field Desorption Mass Spectrometry Analysis) (yield: 81percent).
81% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water; toluene for 10 h; Inert atmosphere; Reflux INTERMEDIATE SYNTHESIS 2-1 (Synthesis of intermediate 2-1)[0105] Under an argon atmosphere, 150 ml of toluene, 150 ml of dimethoxyethane, and 150 ml (300.0 mmol) of a 2M aqueous solution of Na2CO3 were added to a mixture of 28.3 g (100.0 mmol) of 4-iodobromobenzene, 22.3 g (105.0mmol) of dibenzofuran-4-boronic acid, and 2.31 g (2.00 mmol) of Pd[PPh3]4, and the resultant mixture was stirred for10 h while refluxing under heating.[0106] After the reaction, the obtained mixture was cooled to room temperature and extracted with dichloromethanein a separatory funnel. The organic layer was dried over MgSO4, and then filtered and concentrated. The concentratewas purified by silica gel column chromatography to obtain 26.2 g of a white solid, which was identified as the intermediate2-1 by FD-MS analysis (yield: 81percent).
81% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water; toluene for 10 h; Inert atmosphere; Reflux In the argon atmosphere, are respectively weighing 4-iodo-bromobenzene 28.3g (100.0mmol), dibenzofuran-4-boronic acid 22.3g (105.0mmol), Pd[PPh3]42.31g (2.00mmol), adding toluene 150 ml, dimethoxy ethane 150 ml and 2M the Na2CO3aqueous solution 150 ml (300.0mmol), heating to reflux stirring 10 hours.After the reaction, cooling to room temperature, the reaction mixture is transferred to the separatory funnel, using dichloromethane extract. The organic layer using MgSO4dried, filtered and concentrated. The concentrated residue is purified with silica gel column chromatography, thereby obtaining 26.2g white solid (yield 81percent).
81% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water; toluene for 10 h; Inert atmosphere; Reflux Under an argon atmosphere, toluene (150 mL), dimethoxyethane (150 mL), and an aqueous solution of sodium carbonate having a concentration of 2 M (150 mL) were added to 4-iodobromobenzene (28.3 g, 100.0 mmol), dibenzofuran-4-boronic acid (22.3 g, 105 mmol), and tetrakis(triphenylphosphine)palladium(0) (2.31 g, 2.00 mmol), and then the mixture was heated for 10 hours while being refluxed. Immediately after the completion of the reaction, the resultant was filtrated, and then the aqueous layer was removed. The organic layer was dried with sodium sulfate, and was then concentrated. The residue was purified by silica gel column chromatography. Thus, an intermediate body 3H-1 (26.2 g, 81percent yield) was obtained. FD-MS (field desorption mass spectrometry) analysis confirmed that the intermediate had a ratio m/e of 322 with respect to its molecular weight, i.e., 322.
81%
Stage #1: With sodium carbonate In toluene for 0.333333 h;
Stage #2: With tetrakis(triphenylphosphine) palladium(0) In toluene for 4 h; Reflux
To a round bottom flask was added dibenzofuran-4-boronic acid (1.6 g, 5 mmol),4-iodobromobenzene (1.35 g, 4.76 mmol), sodium carbonate (1.48 g, 2M)toluene (50 ml) was added thereto, followed by stirring for 20 minutes. Tetrakis (triphenylphosphine) palladium (0) (0.11 g, 0.095 mmol) was added and the mixture was refluxed for 4 hours.After confirming with HPLC and LC-MASS, the reaction was terminated. After removal of the solvent, it was extracted with MC / H2O. column (MC: Hex = 1: 4) and reprecipitated with MC / hexane to obtain a solid compound (1.24 g, yield = 81percent).
56% With potassium carbonate In ethanol; water; toluene at 70 - 80℃; for 3 h; Preparation of compound C-6-1 [133] After dissolving dibenzo[b,d]furan-4-yl boronic acid (20 g, 94.34 mmol), 1-bromo-4-iodo-benzene (53.4 ml, 188.68 mmol), Pd(PPh3)4 (5.45 g, 4.72 mmol) and K2CO3 (39.1 g, 283.01 mmol) in a mixture of toluene (900mL), EtOH (200mL) and distilled water (200mL), the reaction mixture was stirred for 3 hours at 70~80°C. After terminating the reaction, an aqueous layer was removed from the mixture by a gravity separation. And then, the obtained organic layer was concentrated and purified through column to obtain compound C-6-1 (17 g, 56 percent).
28.5 g With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In toluene at 80℃; for 8 h; Inert atmosphere A three neck flask of 1000 ml was charged with 42.4 g of 4-dibenzofuranboronic acid, 56.0 g of 4-iodobromobenzene, 6.9 g of tetrakis-(triphenylphosphine)palladium (Pd(PPh3)4), 320 mL of a sodium carbonate (Na2CO3) solution of 2M and 320 mL of toluene under argon flow, and then they were reacted at 80° C. for 8 hours. The reaction solution was extracted with toluene/water, and the extract was dried on anhydrous sodium sulfate. This was concentrated under reduced pressure, and a crude product obtained was refined through a column, whereby 28.5 g of a white powder was obtained.
27 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 12 h; Inert atmosphere 20 g (94.4 mmol) of 4-dibenzofuranboronic acid, 28 g (99.2 mmol) of 1-bromo-4-iodobenzene, and 1.08 g (0.94 mmol) of tetrakistriphenylphosphine palladium were dissolved in 240 ml of toluene and 120 ml of ethanol under a nitrogen atmosphere in a flask, 120 ml of an aqueous solution in which 28 g (188.8 mmol) of potassium carbonate was dissolved was added thereto, and the mixture was agitated for 12 hours while being refluxed. When the reaction was complete, the resultant was extracted with ethyl acetate, the extracted solution was dried with magnesium sulfite and filtered, and the filtered solution was concentrated under a reduced pressure. The concentrated product was purified with n-hexane/dichloromethane (9:1 of a volume ratio) through silica gel column chromatography, obtaining 27 g of a white solid compound, an intermediate M-9 (89percent of a yield).
5.92 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 24 h; In the 250 mE rounded-bottom flask, the compoundF 1(3.00 g, 14.15 mmol), the compoundA4 (4.00 g, 14.15mmol), tetrakis(triphenylphosphine)palladium(0) (0.82 g,0.71 mmol) and potassium carbonate (4.84 g, 35.00 mmol)were put into a mixture of toluene (70 mE), ethanol (35 mE)and water (17.5 mE) and stirred under the temperature of100° C. for 24 irs. Afier the completion of the reaction, the mixture was extracted and condensed using water and dichloromethane. The mixture was separated by a column using dichloromethane and n-hexane and precipitated using dichloromethane and petroleum ether. The precipitate was filtered such that the compound F2 was obtained. (5.92 g, 25.29 mmol)
3.95 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 24 h; To a 250 mL round bottom flask was added G1 (3.00 g, 14.15 mmol),G2 (4.00 g, 14.15 mmol), tetrakis (triphenylphosphine) palladium (0) (0.82 g, 0.71 mmol) and potassium carbonate (4.84 g, 35.00 mmol) were dissolved in toluene (80 mL) Ethanol (20 mL) and water (20 mL) were added to the mixed solution,And the mixture was stirred at 100 DEG C for 24 hours. After completion of the reaction,Water and dichloromethane were used for extraction and concentration,The column was separated using dichloromethane and n-hexane.Then, the precipitate was prepared by using dichloromethane and petroleum ether, Filtration gave Compound G3 (3.95 g, 12.22 mmol).
3.95 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 24 h; Dibenzofuran-4-boronic acid (3.00 g, 14.15 mmol), 1-bromo-4-iodobenzene (4.00 g, 14.15 mmol) and tetrakis (triphenylphosphine) palladium (0) (0.82 g, 0.71 mmol) in a 250 mL round- and potassium carbonate (4.84 g, 35.00 mmol) were added to a mixed solution of Toluene (80 mL), Ethanol (20 mL) and water (20 mL) and stirred at 100 ° C for 24 hours. After completion of the reaction, the reaction mixture was extracted with water and dichloromethane, concentrated, and then subjected to column separation using dichloromethane and n-hexane. Thereafter, a precipitate was prepared using dichloromethane and petroleum ether, and filtered to obtain Compound D1 (3.95 g, 12.22 mmol).
3.95 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 24 h; Dibenzofuran-4-boronic acid (3.00 g, 14.15 mmol), 1-bromo-4-iodobenzene (4.00 g, 14.15 mmol), tetrakis (triphenylphosphine) palladium (0) (0.82 g, 0.71 mmol)Potassium carbonate (4.84 g, 35.00 mmol) was dissolved in toluene (80 mL)Was added to a mixed solution of ethanol (20 mL) and water (20 mL), and the mixture was stirred at 100 ° C for 24 hours. After completion of the reaction, the reaction mixture was extracted with water and dichloromethane,The mixture was concentrated, and the column was separated using dichloromethane and n-hexane.Then, the precipitate was prepared by using dichloromethane and petroleum ether,Filtration gave Compound G1 (3.95 g, 12.22 mmol).

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[2] Patent: KR2016/8651, 2016, A, . Location in patent: Paragraph 0155-0157
[3] Patent: KR2016/12846, 2016, A, . Location in patent: Paragraph 0217; 0218; 0219
[4] Patent: KR2015/130221, 2015, A, . Location in patent: Paragraph 0339-0341
[5] Patent: KR101531614, 2015, B1, . Location in patent: Paragraph 0827-0830
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[8] Patent: EP2295421, 2011, A1, . Location in patent: Page/Page column 49
[9] Patent: EP2738166, 2014, A1, . Location in patent: Paragraph 0159-0160
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  • 2
  • [ 100124-06-9 ]
  • [ 106-37-6 ]
  • [ 955959-84-9 ]
YieldReaction ConditionsOperation in experiment
13.7 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; for 5 h; At 80°C, 4-dibenzofuranboronic acid (13.3g), 1,4-dibromobenzene (10g), tetrakis(triphenylphosphine)palladium (3.02g), toluene (158mL), ethanol (65mL), water (65mL), and potassium carbonate (21.69g) were stirred for 5 hours. The reaction was monitored by thin layer chromatography. Upon completion of the reaction, it was quenched with water (100mL) and extracted with ethyl acetate (100mL). The organic layer was extracted with water (3x30mL) and dried over anhydrous sodium sulfate. The ethyl acetate layer was collected through Celite and further purified by column chromatography. Following this, the ethyl acetate layer was evaporated to dryness under vacuum rotavap to yield 13.7g 4-(4'-bromophenyl)dibenzofuran.
Reference: [1] Patent: CN105585555, 2016, A, . Location in patent: Paragraph 0097; 0098
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Chemical Structure| 50548-45-3

[ 50548-45-3 ]

1-Bromodibenzo[b,d]furan

Similarity: 0.92

Chemical Structure| 201138-91-2

[ 201138-91-2 ]

4,6-Dibromodibenzo[b,d]furan

Similarity: 0.91

Chemical Structure| 941710-30-1

[ 941710-30-1 ]

7-Bromochroman

Similarity: 0.87

Chemical Structure| 3875-78-3

[ 3875-78-3 ]

6-Bromochroman

Similarity: 0.85