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[ CAS No. 54523-47-6 ] {[proInfo.proName]}

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Chemical Structure| 54523-47-6
Chemical Structure| 54523-47-6
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Product Details of [ 54523-47-6 ]

CAS No. :54523-47-6 MDL No. :MFCD12031109
Formula : C15H12Br2O Boiling Point : -
Linear Structure Formula :- InChI Key :PQDQAUVBWSUMMB-UHFFFAOYSA-N
M.W : 368.06 Pubchem ID :603327
Synonyms :

Safety of [ 54523-47-6 ]

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:

Application In Synthesis of [ 54523-47-6 ]

* 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 [ 54523-47-6 ]

[ 54523-47-6 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 14062-25-0 ]
  • [ 54523-47-6 ]
YieldReaction ConditionsOperation in experiment
82% With sodium hydride; In toluene; at 30 - 78℃; To a slurry of sodium hydride (9.17 grams, 0.23 mole) in 50 milliliters of toluene was added dropwise, a solution of ethyl 4-bromophenylacetate (50 grams, 0.21 mole) in toluene (50 milliliters) at 30-32C. After addition was completed, the reaction mixture was slowly warmed to 50C where the reaction began to rapidly exotherm with evolution of hydrogen gas. The reaction mixture was further heated to 78C for 2 hours, cooled to room temperature and then HCl (45 grams) in water (22.5 grams) was slowly added dropwise to neutralize the solution. The layers were separated and the aqueous phase was extracted with diethylether. The combined organic extracts were dried and the solvent was removed to leave a yellow oil. This oil was refluxed for 24 hours in a mixture of glacial acid (60 milliliters) and concentrated HCl (30 milliliters). After cooling, the layers were separated, and the organic layer solidified to provide a yellow solid. This crude product was recrystallized from n-heptane to give a pure product as a white solid (31.2 grams, 82% isolated yield).
  • 3
  • [ 4755-77-5 ]
  • [ 589-15-1 ]
  • [ 54523-47-6 ]
  • 4
  • [ 201230-82-2 ]
  • [ 589-15-1 ]
  • [ 19829-56-2 ]
  • [ 54523-47-6 ]
  • [ 88364-54-9 ]
  • [ 1878-68-8 ]
  • 5
  • [ 54523-47-6 ]
  • [ 84-11-7 ]
  • [ 131273-92-2 ]
YieldReaction ConditionsOperation in experiment
60% With potassium hydroxide; In ethanol; at 50℃; for 5h; 1000mL, 3-neck round bottom flask, 2,7-dibromo-phenanthrene-9,10-dione 50 g (0.240 mol), 1,3- bis ((4-bromophenyl) propan-2 one was added 500ml of 80g of ethanol and stirred. In the potassium hydroxide (KOH) in 30g of this solution and stirred for 5 hours at 50 C. The resulting solid was filtered off after cooling the reaction solution to room temperature and washed well with methanol. Vacuum drying the solid obtained to give an intermediate A-1 70 g (yield 60%).
60% With potassium hydroxide; In ethanol; at 50℃; for 5h; 50 g (0.240 mol) of 2,7-dibromophenanthrene-9,10-dione, 1,3-bis (4-boromophenyl) propa-2-one (1000 ml, in a three-neck round bottom flask) 80 g of 1,3-bis (4-bromophenyl) propan-2-one) and 500 ml of ethanol were added and stirred. Potassium hydroxide and 30 g of KOH were added to the solution and stirred at 50 C. for 5 hours. After cooling the reaction solution to room temperature, the resulting solid was filtered and washed well with methanol. The obtained solid was dried in vacuo to give 70 g (yield 60%) of the target compound A.
  • 6
  • [ 25424-26-4 ]
  • [ 54523-47-6 ]
  • [ 54523-26-1 ]
  • 10
  • [ 589-15-1 ]
  • /PBSAB018-1380/ [ No CAS ]
  • [ 19829-56-2 ]
  • [ 54523-47-6 ]
  • [ 88364-54-9 ]
  • [ 1878-68-8 ]
  • 12
  • [ 59965-20-7 ]
  • [ 54523-47-6 ]
  • [ 347390-22-1 ]
  • 14
  • [ 115-77-5 ]
  • [ 54523-47-6 ]
  • [ 493015-32-0 ]
  • 15
  • [ 54523-47-6 ]
  • [ 501034-27-1 ]
  • 16
  • [ 1878-68-8 ]
  • [ 54523-47-6 ]
YieldReaction ConditionsOperation in experiment
68% With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 24h; The DCC (7. 7g, 37. 3mmol) and DMAP (1. 145g, 9. 35mmol) was dissolved in 75ml of dichloromethane was slowly added dropwise to bromophenylacetic acid (8. 05g, 37. 45mmol) in dichloromethane solution 75ml. After the addition was complete the reaction at room temperature for 24h, the solid was filtered off the reaction, dichloromethane was distilled off under reduced pressure, and recrystallized from ethanol to give white crystals 4. 33g, 68% yield.
60% With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 24h;Inert atmosphere; (1) Dicyclohexylcarbodiimide (DCC) (6.19 g, 30 mmol) and 4-dimethylaminopyridine (916 mg, 7.5 mmol) were added to the reaction vessel, pumped three times, and 60 mL of dichloromethane was added under a nitrogen atmosphere. A solution of 4-bromophenylacetic acid (Compound 1, 30 mmol) in dichloromethane (60 mL of dichloromethane) was added dropwise, and reacted for 24 hours after the addition was completed. After the reaction, the solvent was concentrated, removed, separated and purified by column chromatography to obtain intermediate product 2 (compound 2). Yield 60%.
45% With dmap; In dichloromethane; at 20℃; for 24h;Inert atmosphere; To a flame-dried apparatus and under argon, a solution of p-bromophenylacetic acid(5.00 g, 23.3 mmol, 2 equiv) in dry DCM (50 mL) was added to a solution of DCC(4.8 g, 23.3 mmol, 2 equiv) and DMAP (709 mg, 5.8 mmol, 0.5 equiv) in dry DCM(50 mL). The reaction mixture was stirred at room temperature for 24 h. The precipitatewas removed by filtration and the filtrate was evaporated in vacuo. The solid wasrecrystallized from methanol to afford 056 as a light orange solid (1.94 g, 45 %).
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 4h; To a solution of DCC (2.23 g, 10.8 mmol) and DMAP (0.35 g, 2.91 mmol) in anhydrous dichloromethane (50 mL) was slowly added a solution of 2-(4-bromophenyl)acetic acid (366A) (2.0 g, 9.35 mmol) in anhydrous dichloromethane (80 mL). The mixture was stirred at room temperature for 4 hours and concentrated under reduced pressure. The residue was partitioned between EtOAc (50 mL) and water (50 mL). The organic layer was separated, washed with brine (30 mL x 3), dried over anhydrous sodium sulfate, concentrated, and purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 0% to 25% v/v) to afford Compound 366B. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used; -NMR (DMSO-^, 400 MHz): d (ppm) 3.87 (s, 4H), 7.13 (d, J= 8.3 Hz, 4H), 7.49 (d, J= 8.3 Hz, 4H).
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 4h; To a solution of DCC (2.23 g, 10.8 mmol) and DMAP (0.35 g, 2.91 mmol) in anhydrous dichloromethane (50 mL) was slowly added a solution of 2-(4-bromophenyl)acetic acid (366A) (2.0 g, 9.35 mmol) in anhydrous dichloromethane (80 mL). The mixture was stirred at room temperature for 4 hours and concentrated under reduced pressure. The residue was partitioned between EtOAc (50 mL) and water (50 mL). The organic layer was separated, washed with brine (30 mL x 3), dried over anhydrous sodium sulfate, concentrated, and purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 0% to 25% v/v) to afford Compound 366B. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used; 1H-NMR (DMSO-d6, 400 MHz): d (ppm) 3.87 (s, 4H), 7.13 (d, J = 8.3 Hz, 4H), 7.49 (d, J = 8.3 Hz, 4H).

Reference: [1]Doklady Chemistry,2012,vol. 442,p. 23 - 29
[2]Journal of Organic Chemistry,2003,vol. 68,p. 240 - 246
[3]Heterocycles,2013,vol. 87,p. 2333 - 2341
[4]Patent: CN103012098,2016,B .Location in patent: Paragraph 0046; 0047; 0048; 0049
[5]Chemistry - An Asian Journal,2017,vol. 12,p. 3016 - 3026
[6]Patent: CN108752249,2018,A .Location in patent: Paragraph 0040; 0043; 0045; 0053; 0056; 0064; 0065; 0074
[7]Journal of Materials Chemistry C,2017,vol. 5,p. 799 - 802
[8]Angewandte Chemie - International Edition,2020,vol. 59,p. 5712 - 5720
    Angew. Chem.,2020,vol. 132,p. 5761 - 5769,9
[9]Journal of the American Chemical Society,2017,vol. 139,p. 10506 - 10513
[10]Synthesis,2020,vol. 52,p. 2535 - 2540
[11]Journal of the American Chemical Society,2011,vol. 133,p. 20962 - 20969
[12]Turkish Journal of Chemistry,2021,vol. 45,p. 42 - 49
[13]Chemistry - A European Journal,2012,vol. 18,p. 14745 - 14751
[14]Chemical Communications,2015,vol. 51,p. 4477 - 4480
[15]Patent: WO2016/193748,2016,A1 .Location in patent: Page/Page column 22
[16]Journal of the American Chemical Society,2017,vol. 139,p. 17799 - 17802
[17]Chemistry Letters,2007,vol. 36,p. 590 - 591
[18]Journal of Chemical Research,2008,p. 173 - 180
[19]Patent: EP1476416,2015,B1
[20]Patent: WO2019/133770,2019,A2 .Location in patent: Paragraph 001831; 001832; 001833
[21]Patent: WO2020/257487,2020,A1 .Location in patent: Paragraph 001789; 001790
[22]Organic Letters,2021,vol. 23,p. 7295 - 7300
[23]Organic Letters,2021,vol. 23,p. 9425 - 9430
  • 17
  • [ 589-15-1 ]
  • pentacarbonyliron [ No CAS ]
  • [ 54523-47-6 ]
  • 19
  • [ 54523-47-6 ]
  • [ 1226-42-2 ]
  • [ 870249-44-8 ]
YieldReaction ConditionsOperation in experiment
90% With potassium hydroxide; In ethanol; at 70℃; for 3h;Inert atmosphere; (2) Intermediate product 2 (3.69 g, 10 mmol), 4,4'-dimethoxyphenol ester (Compound 3) (2.7 g, 10 mmol) and potassium hydroxide (0.168 g, 3 mmol) were added to the reaction flask, pumped three times, and solvent ethanol (30mL) was injected under nitrogen protection. The resulting mixture was refluxed at 70 C for three hours. After completion of the reaction, the reaction flask was cooled in an ice bath and precipitated to obtain the product. The product was washed with cold ethanol and dried to give red powder product 4 (compound 4). Yield 90%.
  • 20
  • [ 35578-47-3 ]
  • [ 54523-47-6 ]
  • [ 49764-92-3 ]
YieldReaction ConditionsOperation in experiment
68% With potassium hydroxide; In ethanol; dichloromethane; water; Preparative Example 11 2,3,4,5-Tetra(4-bromophenyl)cyclopentadienone (14) A solution of potassium hydroxide (230 mg, 4.1 mmol) in ethanol (5 cm3) was added to a solution of (13) (3.01 g, 8.2 mmol) and <strong>[35578-47-3]4,4'-dibromobenzil</strong> (3.01 g, 8.2 mmol) in ethanol (45 cm3) at 70 C., and the reaction was stirred at 70 C. for 4 hours. Water (200 cm3) and dichloromethane (200 cm3) were added, and the layers were separated. The organic layer was washed with brine (200 cm3) and dried over magnesium sulfate. The solvent was removed to leave a dark purple solid. The crude product was passed through a plug of silica, and then recrystallized from a dichloromethane/ethanol mixture to give (14) as a dark purple crystalline solid (3.87 g, 68%).
62% With potassium hydroxide; In ethanol; for 0.666667h;Reflux; To a solution of 056 (310 mg, 0.84 mmol, 1 equiv) and 101 (310 mg, 0.84 mmol, 1 equiv) in ethanol (3 mL) was added a solution of KOH (47 mg, 0.84 mmol, 1 equiv) in ethanol (0.5 mL). The reaction mixture was stirred at reflux for 40 mm. The dark redsolution was then cooled down to 0 00. The resulting dark red precipitate was filtered and washed with cold ethanol, affording 102 as dark red crystals (365 mg, 62 %).
After 4,4v-dibromobenzyl (9.8 g, 27 mmol) and di(4-bromophenyl)acetone (2.0 g,5.4 mmol) were dissolved in 40 mL of ethanol and heated, the mixture was refluxed under stirring for 1 hour. KOH (0.3 g, 5.4 mmol) dissolved in 10 mL of ethanol was slowly added dropwise thereto, and then refluxed under stirring for 30 minutes. The resultant was slowly cooled to give a dark red solid powder. The obtained dark red <n="35"/>solid powder was filtered under reduced pressure, and then dried under vacuum to obtain a starting material represented by Formula k. [114] MS [M+H] 700
  • 21
  • [ 54523-47-6 ]
  • [ 6217-22-7 ]
  • [ 908352-01-2 ]
  • 22
  • [ 54523-47-6 ]
  • [ 189619-30-5 ]
  • 2,5-bis(4-bromophenyl)-3,4-(4-triisopropysilylethynylphenyl)cyclopenta-2,4-dien-1-one [ No CAS ]
  • 24
  • [ 54523-47-6 ]
  • [ 134-81-6 ]
  • [ 54523-24-9 ]
YieldReaction ConditionsOperation in experiment
91% With potassium hydroxide; In methanol; dichloromethane; for 1.5h;Inert atmosphere; Reflux; To a solution of <strong>[54523-47-6]1,3-bis(4-bromophenyl)-2-propanone</strong> (3 300 mg, 0.815 mmol) and benzyl (0.815 mmol) in dichloromethane (1.5 mL)(30 mL) was added potassium hydroxide (22.8 mg, 0.407 mmol) as a solution in methanol (3 mL). the reaction was heated to reflux under nitrogen for 90 minutes before cooling in an ice bath. This mixture was introduced into 50 mL of cold methanol, and the obtained solid 2,5-bis(4-bromophenyl)-3,4-diphenylcyclopenta-2,4-dienone (4) was filtered to obtain a dark purple solid (404 mg, 91% yield).
68% After benzyl (1.14 g, 5.4 mmol) and di(4-bromophenyl)acetone (2.0 g, 5.4 mmol) were dissolved in 40 mL of ethanol and heated, the mixture was refluxed under stirring <n="34"/>for 1 hour. KOH (0.3 g, 5.4 mmol) dissolved in 10 mL of ethanol was slowly added drop wise thereto, and then refluxed under stirring for 30 minutes. The resultant was slowly cooled to give a dark red solid powder. The obtained dark red solid powder was filtered under reduced pressure, and then dried under vacuum to obtain a starting material represented by Formula i.[104] (2.0 g, 68 %); 1H NMR (400 MHz, DMSO-J ) 7.50-7.48(d, 4H), 7.30-7.23(m, 6H),7.11-7.09(d, 4H), 6.98-6.96(d, 4H) ; MS [M+H] 540,542,544
  • 25
  • [ 54523-47-6 ]
  • [ 917974-57-3 ]
  • 26
  • [ 54523-47-6 ]
  • C36H23Br5 [ No CAS ]
  • 27
  • [ 54523-47-6 ]
  • 1-bromo-1-(p-tolyl)-2,3,4,5-tetra(4-bromophenyl)cyclopenta-2,4-diene [ No CAS ]
  • 28
  • [ 54523-47-6 ]
  • C36H23Br5 [ No CAS ]
  • 29
  • [ 54523-47-6 ]
  • 9,12-bis-(4-bromo-phenyl)-10-phenanthren-4-yl-benzo[e]pyrene [ No CAS ]
  • 30
  • [ 54523-47-6 ]
  • [ 908352-03-4 ]
  • 32
  • [ 54523-47-6 ]
  • [ 870249-48-2 ]
  • 33
  • [ 54523-47-6 ]
  • [ 870249-47-1 ]
  • 34
  • [ 54523-47-6 ]
  • C90H64N2O4 [ No CAS ]
  • 35
  • [ 54523-47-6 ]
  • C96H76N2O2 [ No CAS ]
  • 36
  • [ 54523-47-6 ]
  • [ 493015-33-1 ]
  • 38
  • [ 54523-47-6 ]
  • 2-methyl-4,6-bis(4-bromophenyl)-1,2,3-triazin-5(2H)-one [ No CAS ]
  • 39
  • [ 54523-47-6 ]
  • [ 501034-31-7 ]
  • 45
  • [ 54523-47-6 ]
  • [ 158230-11-6 ]
  • 46
  • [ 1123311-64-7 ]
  • [ 54523-47-6 ]
  • [ 1123311-65-8 ]
  • 47
  • [ 849023-56-9 ]
  • [ 54523-47-6 ]
  • [ 1253523-59-9 ]
  • 48
  • [ 54523-47-6 ]
  • [ 1319733-03-3 ]
  • 49
  • [ 54523-47-6 ]
  • [ 82-86-0 ]
  • 7,9-bis(4-bromophenyl)-8H-cyclopenta[a]acenaphthylen-8-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With potassium hydroxide; In ethanol; at 85℃; for 48h; Acenaphthenequinone (6.9 g, 38 mmol) and 1,3-bis (4-bromophenyl) propan-2-one (14 g, 38 mmol) was added to ethanol (300 mL), then potassium hydroxide (KOH) (6.4 g, 114 mmol) was added and the mixture was stirred and refluxed at 85 C. for 48 hours. After lowering the temperature to ordinary temperature and adding 200 mL of water, the produced solid was filtered and then dried to produce [Compound B-1] (17.3 g, yield 88%).
30% With potassium hydroxide; In ethanol; for 24h;Inert atmosphere; Reflux; Synthesis of 2 was performed according to the published description in the literature [32]. The mixture containing 2.09 g(5 mmol) of compound 1 and 0.91 g (5 mmol) of acenaphthylene-1,2-dione was heated up to the reflux temperature in dryethanol. Then, the reaction was sustained by adding a solution of KOH (1.5 M) over 5 min. The reaction color changed todark green after 10 min and it refluxed for 24 h. For the purpose of purification, the flask content was filtered and the crudeproduct was washed with cold toluene several times to yield 30% of compound 2 as a dark green solid. m.p. 400-405 C;Anal. Calcd. for C27H14Br2O(514.22): C, 63.07; H, 2.74; Br, 31.08; O,3.11. Found: C, 63.21; H, 2.88.
  • 50
  • [ 36635-61-7 ]
  • [ 589-15-1 ]
  • [ 54523-47-6 ]
  • 51
  • C18H16Br2O3 [ No CAS ]
  • [ 54523-47-6 ]
  • 53
  • [ 54523-47-6 ]
  • [ 1692-15-5 ]
  • [ 1352050-04-4 ]
  • 54
  • [ 223707-22-0 ]
  • [ 54523-47-6 ]
  • [ 1393377-89-3 ]
  • 55
  • [ 579-39-5 ]
  • [ 54523-47-6 ]
  • [ 1393377-87-1 ]
  • 57
  • [ 54523-47-6 ]
  • [ 73790-20-2 ]
  • [ 1393377-88-2 ]
  • 58
  • [ 54523-47-6 ]
  • [ 1386995-51-2 ]
  • 59
  • [ 54523-47-6 ]
  • 1,9,10-tris(4-bromophenyl)-2,3,7,8-tetrakis(4-butylphenyl)-5,5-difluoro-5H-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinin-4-ium-5-uide [ No CAS ]
  • 60
  • [ 54523-47-6 ]
  • 1,9,10-tris(4-bromophenyl)-5,5-difluoro-2,3,7,8-tetraphenyl-5H-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinin-4-ium-5-uide [ No CAS ]
  • 61
  • [ 54523-47-6 ]
  • C51H33Br3N2 [ No CAS ]
  • 62
  • [ 54523-47-6 ]
  • 1,2-bis-(4-butylphenyl)ethane-1,2-dione [ No CAS ]
  • [ 1386995-50-1 ]
  • 64
  • [ 16218-32-9 ]
  • [ 54523-47-6 ]
  • [ 1425336-57-7 ]
  • 65
  • [ 485-47-2 ]
  • [ 54523-47-6 ]
  • 1,3-di(4-bromphenyl)indeno[a]cyclopenta-2,8-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
81.5% With potassium hydroxide; In methanol; ethanol; at 75℃; for 3h; The ninhydrin (2 · 86g, 14. 65mmol) and 1,3-bis (4-bromophenyl) -2-propanone (4. 996g, 13. 65mmol) was dissolved in hot ethanol 20ml, was slowly added dropwise plus 3. 5ml 10% KOH / MeOH solution, after completion of the dropwise addition under stirring for 3h at 75, until the solution stops the reaction from yellow to dark brown, the reaction was filtered and the resulting solid, recrystallized from ethanol, to give brown crystals 5 · 45g yield 81.5%
  • 66
  • [ 54523-47-6 ]
  • [ 121392-37-8 ]
  • 67
  • [ 54523-47-6 ]
  • 4,4''''-dimethoxy-2'',3'',5'',6'''-tetraphenyl-1,1':4',1'':4'',1''':4''',1''''-quinquephenyl [ No CAS ]
  • 68
  • [ 54523-47-6 ]
  • 2'',3''',5'',6''-tetraphenyl-[1,1':4',1'':4'',1''':4''',1''''-quinquephenyl]-4,40000-diol [ No CAS ]
  • 69
  • [ 869589-06-0 ]
  • [ 54523-47-6 ]
  • 1,3-bis (4-(2-decyltetradecyl) phenyl) propan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% To 1,3-bis(4-bromophenyl)-propan-2-one 7b (2.00 g, 5.43 mmol) and dichloro[1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) (0.384 g, 0.544 mmol) in a 100-mL Schlenk flask was added via cannula the solution of dodecylzinc bromide. The reaction mixture was stirred at room temperature for 18 h, and then quenched by hydrochloric acid (2 M, 40 mL). The aqueous layer was extracted three times with dichloromethane. The combined organic extracts were washed three times with water, dried over sodium sulfate, and evaporated. The crude material was purified by silica gel column chromatography (eluent: 20% dichloromethane/hexane) to give the title compound as pale yellow oil (4.13 g, 86% yield). 1H NMR (300 MHz, CD2Cl2) □: δ 0.88 (t, J=6.7 Hz, 12H), 1.16-1.37 (m, 80H), 1.55-1.67 (m, 2H), 2.50 (d, J=7.0 Hz, 4H), 3.68 (s, 4H), 7.01 (d, J=8.1 Hz, 4H), 7.09 (d, J=8.1 Hz, 4H). 13C NMR (75 MHz, CD2Cl2): δ 14.36 (4C), 23.18 (4C), 26.99 (4C), 29.85 (4C), 30.16 (16C), 30.50 (4C), 32.42 (4C), 33.60 (4C), 40.12 (2C), 40.57 (2C), 49.13 (2C), 129.70 (4C), 129.86 (4C), 131.88 (2C), 141.11 (2C), 206.30. Elemental Analysis: Calc. for C63H110O: C, 85.64; H, 12.55. Found: C, 85.71; H, 12.45.
86% Dry N,N-dimethylacetamide (10 mL) was added to zinc (3.21 g,49.1 mmol) and iodine (0.689 mg, 2.71 mmol) in a 100-mL two-necked flaskequipped with a condenser, and stirred at room temperature until the purplecolor of iodine disappeared. 2-decyl-tetradecylbromide (15.3 g, 36.7 mmol) wasthen added to the mixture and stirred at 80 C for 24 h to generate dodecylzincbromide. the above solution of dodecylzinc bromide was added via cannula to1,3-bis(4-bromophenyl)-propan-2-one 7b (2.00 g, 5.43 mmol) anddichloro[1,1′-bis(diphenylphosphino)-ferrocene]palladium(II) (0.384 g, 0.544mmol) in a 100-mL Schlenk flask. The reaction mixture was stirred at roomtemperature for 18 h, and then quenched by hydrochloric acid (2 M, 40 mL). Theaqueous layer was extracted three times with dichloromethane. The combinedorganic extracts were washed three times with water, dried over sodium sulfate,and evaporated. The crude material was purified by silica gel columnchromatography (eluent: 20% dichloromethane/hexane) to give the title compoundas pale yellow oil (4.13 g, 86% yield).
  • 70
  • [ 3457-48-5 ]
  • [ 54523-47-6 ]
  • C31H22Br2O [ No CAS ]
  • 71
  • [ 54523-47-6 ]
  • [ 1058140-98-9 ]
  • C45H36Br2O3 [ No CAS ]
  • C60H48Br2O4 [ No CAS ]
  • C75H60Br2O5 [ No CAS ]
  • 72
  • [ 54523-47-6 ]
  • [ 536-74-3 ]
  • [ 582323-25-9 ]
YieldReaction ConditionsOperation in experiment
71% With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 80℃; for 20.25h;Inert atmosphere; In a 250 ml flask was placed 18.4 grams (0.05 mole) of 1,3-bis-(4-bromophenylphenyl)-2-propanone, 24 grams (0.24 mole) of triethylamine, 12 grams (0.12 mole) of phenylacetylene, and 60 milliliters of N, N-dimethylformamide. The reaction mixture was purged with nitrogen for 15 minutes then 0.60 gram (0.0023 mole) of triphenylphosphine and 0.08 gram (0.00036 mole) of palladium acetate were added. After heating the reaction mixture at 80C under a nitrogen atmosphere for 20 hours, the flask was allowed to cool to room temperature, then water (200 milliliters) and toluene (200 milliliters) were added. The resulting organic layer was washed with 10% aqueous HCl, water and saturated aqueous NaCl then dried over anhydrous Na2SO4. The pure product (14.5 grams) was obtained upon removal of the toluene and recrystallization from toluene/hexanes in 71% isolated yield.
  • 73
  • [ 54523-47-6 ]
  • C15H10Br4O [ No CAS ]
  • 74
  • [ 54523-47-6 ]
  • C15H11Br3O [ No CAS ]
  • 75
  • [ 54523-47-6 ]
  • C15H12Br2N6O [ No CAS ]
  • 76
  • [ 54523-47-6 ]
  • C23H18Br2N6O2 [ No CAS ]
  • 77
  • [ 54523-47-6 ]
  • C23H16Br2N8O2 [ No CAS ]
  • 78
  • [ 54523-47-6 ]
  • C23H16Br2N4O2 [ No CAS ]
  • 79
  • [ 54523-47-6 ]
  • 1,4-bis(4-bromophenyl)-2-trimethylsilyltriphenylene [ No CAS ]
  • 82
  • [ 54523-47-6 ]
  • 1-(3-iodophenyl)-2-pheylethane-1,2-dione [ No CAS ]
  • 2,5-bis(4-bromophenyl)-3-(3-iodophenyl)-4-phenylcyclopenta-2,4-dien-1-one [ No CAS ]
  • 83
  • [ 54523-47-6 ]
  • 1,2-bis(4-mesitylphenyl)ethane-1,2-dione [ No CAS ]
  • C47H38Br2O [ No CAS ]
  • 84
  • [ 37859-24-8 ]
  • [ 589-15-1 ]
  • [ 54523-47-6 ]
YieldReaction ConditionsOperation in experiment
41 mmol With bis(1,5-cyclooctadiene)nickel(0); magnesium chloride; zinc; In acetonitrile; at 20℃; for 12h;Inert atmosphere; To a three-necked flask just from the blast oven, add 1-bromo-4- (bromomethyl) benzene 100 mmol, anhydrous1.5 equivalents of magnesium chloride, 0.15 equivalents of ligand bipyridine, 3 equivalents of activated zinc powder. Under nitrogen protection, Ni (COD) 2 0.1 was addedEquivalent, followed by the addition of a solvent acetonitrile, and 2- (4-bromophenyl) acetyl chloride. Reaction at room temperature for 12 h. Reaction finishedAfter completion, the product was subjected to column chromatography to give 41 mmol (2-1)
  • 85
  • [ 54523-47-6 ]
  • [ 95-92-1 ]
  • C17H10Br2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
37 mmol With sodium; In ethanol; at 0 - 20℃; for 51h; 9.2 g of metallic sodium was dissolved in 185 ml of absolute ethanol, the solution was cooled to 0 C,42 g of diethyl oxalate and 30 g of diethyl oxalate. The reaction solution was allowed to react at 0 C for 3 hours and gradually warmed to room temperature for 48 h. The reaction is completeAfter the gradual drop of glacial acetic acid to the reaction solution neutral. The reaction solution passes through a diatomaceous earth funnel to remove a small amount of oil. Drop 100ml2N concentrated sulfuric acid, with bright yellow solid produced. Filter, filter cake washed with water. dry. The crude product was recrystallized three times with xyleneEthanol was recrystallized twice to give pale yellow needles, 37 mmol (2-2)
Same Skeleton Products
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