Alternatived Products of [ 669767-20-8 ]
Product Details of [ 669767-20-8 ]
| CAS No. : | 669767-20-8 |
MDL No. : | MFCD28404221 |
| Formula : |
C8H6Br2O2
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
293.94
|
Pubchem ID : | - |
| Synonyms : |
|
Safety of [ 669767-20-8 ]
Application In Synthesis of [ 669767-20-8 ]
* 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 [ 669767-20-8 ]
- 1
-
[ 909389-74-8 ]
-
[ 669767-20-8 ]
| Yield | Reaction Conditions | Operation in experiment |
| 81.25% |
With aluminum (III) chloride at 160℃; for 3h; Inert atmosphere; |
XLVIII
A stirred solution of compound XLVIII-2 (8.00 g, 54.43 mmol) and A1C13 (7.26 g, 54.43 mmol) was heated to 160 °C for 3 hours under argon. The solution was quenched with water, extract with EtOAc (60 mL x 3), the combined organic layers were dried over Na2S04, concentrated in vacuo, and purified by chromatography (PE:EA = 50: 1) to afford compound XLVIII-3 (6.5 g, yield 81.25%). 1H NMR (400MHz, DMSO-d6) ^10.94 (s, 1 H), 7.32 (s, 1H), 7.07 (s, 1 H), 2.43 (s, 3 H). |
- 2
-
[ 50562-79-3 ]
-
[ 669767-20-8 ]
-
C24H17Br2NO4S
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: 2',4'-dibromo-6'-hydroxyacetophenone With sodium hydroxide In methanol; water at 20℃; for 0.5h;
Stage #2: 1-(4-tolylsulfonyl)indole-3-carboxaldehyde In methanol; water at 20℃; |
3.1 Synthesis of brominated 3-hydroxy-2-phenylchromone derivatives (1-14) & synthesis of brominated 2-phenylchromone derivatives (15-28)
General procedure: A mixture of 3,5-dibromo-2-hydroxyacetophenone (294 mg, 1.0 mmol) and 5.0 mL aqueous NaOH solution (30%) was dissolved in 15.0 mL distilled MeOH and stirred for 30 min at ambient temperature followed by the addition of substituted aromatic aldehyde (1.0 mmol) dropwise (solution prepared in 1-2 mL methanol) and the reaction mixture was further stirred for 2-3 h at the same temperature. The progress of the formation of chalcone was monitored by comparative TLC using n-hexane: ethyl acetate (3:1) as a mobile phase. After completion of the reaction (indicated by TLC), the contents of the reaction mixture were then acidified by dilute HCl (10%) and poured over ice-cold water. The solid obtained was filtered, washed with water and eventually recrystallized from ethanol to afford the pure product. In the first route, the resultant chalcones (in situ) so formed were converted into corresponding substituted 3-hydroxyflavone derivatives by conventional Algar-Flynn-Oyamada (AFO) conditions upon oxidative cyclization using H2O2 (35%) in methanol and allowed it to stir for a further 1 h at the same temperature. In the second route, the appropriate substituted chalcone (1.0 mmol), I2 (254 mg, 1.0 mmol) was dissolved in DMSO(10 mL). The mixture was refluxed at 130 °C for 3-5 h. Upon reaction completion, as indicated by TLC, the solution was cooled to room temperature and poured onto crushed ice and sodium thiosulphate solution (10% Na2S2O3, 10 mL) was added to the reaction mixture followed by an excessive amount of water to allow precipitation. The product was rinsed and allowed to dry at room temperature and the solid was recrystallized from ethanol to afford pure flavone. |
Reference：
[1]Ashraf, Jamshaid; Mughal, Ehsan Ullah; Alsantali, Reem I.; Obaid, Rami J.; Sadiq, Amina; Naeem, Nafeesa; Ali, Anser; Massadaq, Anam; Javed, Qamar; Javid, Asif; Sumrra, Sajjad Hussain; Zafar, Muhammad Naveed; Ahmed, Saleh A.
[Bioorganic and Medicinal Chemistry, 2021, vol. 35]
Chemistry
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Material Science
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110K+ Compounds
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