Alternatived Products of [ 13997-74-5 ]
Product Details of [ 13997-74-5 ]
| CAS No. : | 13997-74-5 |
MDL No. : | MFCD00297344 |
| Formula : |
C9H9BrO
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
213.07
|
Pubchem ID : | - |
| Synonyms : |
|
Safety of [ 13997-74-5 ]
| Signal Word: | |
Class: | |
| Precautionary Statements: | |
UN#: | |
| Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 13997-74-5 ]
* 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 [ 13997-74-5 ]
- Downstream synthetic route of [ 13997-74-5 ]
- 1
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[ 13997-74-5 ]
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[ 197577-35-8 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: m-CPBA / CH2Cl2 / Heating
2: methanesulfonic acid / CH2Cl2 / 20 °C |
|
|
Multi-step reaction with 2 steps
1: m-chloroperbenzoic acid / CH2Cl2 / 24 h / 10 - 20 °C
2: Kieselgel 60 / CH2Cl2 / 24 h / Ambient temperature |
|
|
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane at 70℃; for 6h; |
15.1
To 2-allyl-4-bromophenol (3.13 g, 14.6 mmol) in 1,2-dichloroethane (250 ml) add rmchloroperbenzoic acid (70%, 3.59 g, 14.5 mmol). Heat to 70° C., stir 4 h, and add more peracid (2.50 g). Heat an additional 2 h, allow to cool, concentrate, and partition with ether and 1N NaOH. Dry (MgSO4) and concentrate to obtain the alcohol as a yellow oil. |
Reference：
[1]Sviridov, Sergey I.; Vasil'ev, Andrei A.; Sergovskaya, Natalia L.; Chirskaya, Marina V.; Shorshnev, Sergey V.
[Tetrahedron, 2006, vol. 62, # 11, p. 2639 - 2647]
[2]Chapleo, Christopher B.; Myers, Peter L.; Butler, Richard C. M.; Davis, John A.; Doxey, John C.; et al.
[Journal of Medicinal Chemistry, 1984, vol. 27, # 5, p. 570 - 576]
[3]Current Patent Assignee: MERCK & CO INC - US2005/239795, 2005, A1
Location in patent: Page/Page column 16
- 2
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[ 13997-74-5 ]
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[ 3875-78-3 ]
- 3
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[ 5544-60-5 ]
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[ 13997-74-5 ]
-
[ 566202-90-2 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3h;Inert atmosphere; |
[Example 3] Synthesis of 2-allyl-1-(4-benzyloxy-benzyloxy)-4-bromobenzene (compound 4); Under an atmosphere replaced with argon, 2-allyl-4-bromophenol (compound 3), potassium carbonate and benzyloxy-benzylchloride (BnBr) were dissolved in dimethylformamide (DMF), and stirred at room temperature for 3 hours. After confirming that the starting materials were disappeared using thin-layer chromatography (TLC) (with a developer of n-hexane:ethyl acetate = 4:1), the reaction liquid was subjected to extraction using 20mL of water and 20mL of ethyl acetate. The organic phase was washed with 20mL of water twice, dried using magnesium sulfate, and then subjected to filtration. The filtrate was concentrated under reduced pressure using an evaporator. The resultant residue was subjected to purification using silica gel flash chromatography (silica gel flash c.c.) (with a developer of n-hexane:ethyl acetate = 4:1), to thereby obtain 2-allyl-1-(4-benzyloxy-benzyloxy)-4-bromobenzene (compound 4) as light brown solid. |
- 4
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[ 7648-30-8 ]
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[ 13997-74-5 ]
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ethyl-3-(5-bromo-2,3-dihydrobenzofuran-2-yl)-2,2-difluoropropanoate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 80% |
With 1,4-diaza-bicyclo[2.2.2]octane; fac-tris(2-phenylpyridinato-N,C2')iridium(III) In acetonitrile at 20℃; for 12h; Schlenk technique; Irradiation; Inert atmosphere; |
|
| 76% |
With N,N'-dimethylpiperazine In 1,4-dioxane at 80℃; Inert atmosphere; Schlenk technique; |
2: General Procedure for the synthesis of 4 and 6.
General procedure: To a 25 mL of Schlenk tube equipped with a Teflon septum, dioxane (2.0 mL), 1,4 dimethylpiperazine (0.9 mmol, 3.0 equiv), ICF2COOEt (2) (0.9 mmol, 3.0 equiv) and 1 or 5 (0.3 mmol) were added subsequently under Ar. The solution was stirred at 80 °C in an oil bath for 12 24 h. After the reaction was finished, solvent was removed and the concentrated residue was purified by column chromatography over silica gel to afford the desired products 4 and 6. |
| 75% |
With 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium(0); potassium acetate In 1,4-dioxane at 80℃; for 20h; Sealed tube; Inert atmosphere; Schlenk technique; chemoselective reaction; |
|
| 75% |
With 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium(0); potassium acetate In 1,4-dioxane at 80℃; for 20h; Sealed tube; |
3
In a 25 ml sealed tube reaction flask ,added 0.15 mmol of 4-bromo -2-allylphenol, 0.3 mmol of iodo-difluoroacetate, 0.0075mmol of Tetrakis(triphenylphosphine)palladium , 0.015mmol of 1,1-bis(diphenylphosphino) ferrocene,0.3mmol of potassium acetate and 2 ml of 1,4-dioxane, and the reaction system was stirred at 80 ° C for C 20 hours, then stop heating and stirring and cooled to room temperature. Ethyl acetate to extract the reaction solution, and the solvent was removed by steaming under reduced pressure, and then purified by column chromatography to obtain the target product. The column chromatography eluent used was a 100: 1 by volume petroleum ether: ethyl acetate mixed solvent in 75% yield |
Reference：
[1]Liao, Jianhua; Ouyang, Lu; Lai, Yinlong; Luo, Renshi
[Journal of Organic Chemistry, 2020, vol. 85, # 8, p. 5590 - 5597]
[2]Ma, Ming-Jian; Jia, Jia; Yan, Guoming; Yin, Chao; Yu, Wei; Guo, Peng; Zhao, Liang; He, Chun-Yang
[Tetrahedron Letters, 2020, vol. 61, # 50]
[3]Liao, Jianhua; Fan, Lianfeng; Guo, Wei; Zhang, Zhenming; Li, Jiawei; Zhu, Chuanle; Ren, Yanwei; Wu, Wanqing; Jiang, Huanfeng
[Organic Letters, 2017, vol. 19, # 5, p. 1008 - 1011]
[4]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN106565648, 2017, A
Location in patent: Paragraph 0046; 0047
- 5
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[ 7648-30-8 ]
-
[ 13997-74-5 ]
-
ethyl 5-(5-bromo-2-hydroxyphenyl)-2,2-difluoro-4-iodopentanoate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 89% |
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; bis-diphenylphosphinomethane In tetrahydrofuran at 80℃; for 20h; Inert atmosphere; |
34 Example 34
To a 25 mL reaction tube, 11.5 mg (10 mol%) of DPPM was added, three times of argon was substituted, and then 2 mL of tetrahydrofuran (THF) was added, and 46 μL (0.30 mmol, 1 equivalent) of Compound D-9 was injected, and 88 μL (0.60 mmol) of Compound B was injected. After stirring at 80 ° C for 20 hours, the compound E-9 was obtained in a yield of 89%. |
| 89% |
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; bis-diphenylphosphinomethane In tetrahydrofuran at 80℃; for 20h; Inert atmosphere; Schlenk technique; |
|
Reference：
[1]Current Patent Assignee: ZUNYI MEDICAL UNIVERSITY - CN110172022, 2019, A
Location in patent: Paragraph 0116; 0117; 0118
[2]Zhao, Liang; Huang, Yang; Wang, Ze; Zhu, Erlin; Mao, Ting; Jia, Jia; Gu, Jiwei; Li, Xiao-Fei; He, Chun-Yang
[Organic Letters, 2019, vol. 21, # 17, p. 6705 - 6709]
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