Alternatived Products of [ 397-54-6 ]
Product Details of [ 397-54-6 ]
| CAS No. : | 397-54-6 |
MDL No. : | |
| Formula : |
C13H8FNO
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
213.21
|
Pubchem ID : | - |
| Synonyms : |
|
Safety of [ 397-54-6 ]
| Signal Word: | |
Class: | |
| Precautionary Statements: | |
UN#: | |
| Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 397-54-6 ]
* 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 [ 397-54-6 ]
- 1
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[ 456-22-4 ]
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[ 95-55-6 ]
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[ 397-54-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 85% |
With Amberlyst-15 In water at 90℃; for 1h; Irradiation; |
General procedure for the preparation of compound 3-5
General procedure: To a solution of o-phenylenediamine 1a, o-amino phenol 1b or o-amino thiophenol 1c (1.0 mmol) and aromatic acid (2, 1.2 mmol) in water (5 mL) was added Amberlyst-15 (10%, w/w) and the mixture was irradiated with ultrasound (40 KHz) continuously at 90 °C till the completion of the reaction(monitored by TLC) as indicated in Table 3. The solid separated was filtered, washed with diethyl ether (2 x 5 mL), dried and treated with EtOAc (15 mL). After stirring for 10 min the mixture was filtered to remove the insoluble catalyst. The filtrate was collected and concentrated under vacuum. The solid obtained was purified by recrystallization (column chromatography infew cases) to afford the desired products 3, 4 or 5. |
| 56.6% |
With polyphosphoric acid at 160℃; for 5h; |
1 Synthesis of Intermediate 1
Add 4-fluorobenzoic acid (5g, 35.7mmol), 2-aminophenol (3.9g, 35.7mmol) and 20g polyphosphoric acid in the flask, and react at 160°C for 5 hours.After cooling to 80-90°C, 50 mL of water was added dropwise, the precipitated solid was filtered, washed with water to neutral, then rinsed with ethanol, and dried. The crude product was separated by column chromatography to obtain 4.2 g of white solid with a yield of 56.6%. |
| 56.6% |
With polyphosphoric acid at 160℃; for 5h; |
|
| 56.6% |
With polyphosphoric acid at 160℃; for 5h; |
1 Synthesis of Intermediate 1
Add 4-fluorobenzoic acid (5g, 35.7mmol) in the flask, 2-aminophenol (3.9g, 35.7mmol) and 20g polyphosphoric acid were reacted at 160°C for 5 hours, after cooling to 80-90°C, 50 mL of water was added dropwise, the precipitated solid was filtered, washed with water to neutral, then rinsed with ethanol, and dried. The crude product was separated by column chromatography to obtain 4.2 g of white solid with a yield of 56.6%. |
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With PPA at 250℃; |
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With polyphosphoric acid at 150℃; for 5h; |
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Reference：
[1]Rambabu; Murthi, P. Radha Krishna; Dulla, Balakrishna; Basaveswara Rao; Pal, Manojit
[Synthetic Communications, 2013, vol. 43, # 22, p. 3083 - 3092]
[2]Current Patent Assignee: BAIKE BIOTECH (SHANGHAI) CO LTD; SHANXI HUAHUI OPTOELECTRONICS TECHNOLOGY CO LTD - CN112778293, 2021, A
Location in patent: Paragraph 0042-0045
[3]Gao, Zhixiang; Huang, Jinhai; Jin, Xin; Miao, Yanqin; Su, Jianhua; Tian, He; Wang, Hua; Yin, Mengna; Zhao, Zhenhong; Zhou, Haitao
[Journal of Materials Chemistry C, 2021, vol. 9, # 18, p. 5899 - 5907]
[4]Current Patent Assignee: BAIKE BIOTECH (SHANGHAI) CO LTD; SHANXI HUAHUI OPTOELECTRONICS TECHNOLOGY CO LTD - CN112851655, 2021, A
Location in patent: Paragraph 0049-0052
[5]Bystrov,V.F. et al.
[Journal of general chemistry of the USSR, 1968, vol. 38, p. 963 - 966][Zhurnal Obshchei Khimii, 1968, vol. 38, p. 1001 - 1005]
[6]Leng, Yuting; Yang, Fan; Zhu, Weiguo; Wu, Yangjie; Li, Xiang
[Organic and Biomolecular Chemistry, 2011, vol. 9, # 14, p. 5288 - 5296]
- 2
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[ 273-53-0 ]
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[ 352-34-1 ]
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[ 397-54-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 90% |
With lithium tert-butoxide In N,N-dimethyl-formamide at 140℃; for 0.166667h; |
|
| 86% |
With bis(triphenylphosphine)copper(I) cyanide; caesium carbonate; triphenylphosphine for 24h; Reflux; |
|
Reference：
[1]Do, Hien-Quang; Daugulis, Olafs
[Journal of the American Chemical Society, 2007, vol. 129, # 41, p. 12404 - 12405]
[2]Kim, Donghae; Yoo, Kwangho; Kim, Se Eun; Cho, Hee Jin; Lee, Junseong; Kim, Youngjo; Kim, Min
[Journal of Organic Chemistry, 2015, vol. 80, # 7, p. 3670 - 3676]
- 3
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[ 10025-83-9 ]
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[ 123-54-6 ]
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[ 397-54-6 ]
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[ 859161-70-9 ]
- 4
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[ 273-53-0 ]
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[ 824-80-6 ]
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[ 397-54-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 76% |
|
General procedure: Under nitrogen atmosphere, a sealable reaction tube equipped with a magnetic stirrer bar was charged with azole (0.50 mmol), sodium arylsulfinate (1.0 mmol), Pd(OAc)2 (0.025 mmol), Cu(OAc)2 (1.0 mmol), CF3COOH (0.50 mmol), and dimethylglycol (2.0 mL). The rubber septum was then replaced by a Teflon-coated screw cap, and the reaction vessel placed in an oil bath at 120 C for 24 h. After the reaction was completed, it was cooled to room temperature and the mixture was treated with K2CO3 solution (1.0 mol/L, 3.0 mL), then extracted with ethyl acetate. The resulting solution was dried by Na2SO4 then concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluant: petroleum ether/ethyl acetate=12:1, v/v) to give the desired product. |
- 5
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[ 273-53-0 ]
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[ 403-43-0 ]
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[ 397-54-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 92% |
With hafnium-based metal-organic framework catalyst In neat (no solvent) at 170℃; for 6h; |
3.3. Procedure of 2-arylbenzoxazoles derivatives
General procedure: A mixture of VNU-11(Hf) (0.018 g, 0.01 mmol), aromatic acylchloride (0.140 g, 1 mmol) and benzoxazole (0.119 g, 1 mmol)was heated at 170 C under conventional heating for a few hoursor microwave irradiation of a CEM Discover apparatus for a fewminutes. After completion of reaction, the catalyst was filteredfrom the reaction mixture. The filtrate was diluted with ethyl acetate (50 mL), washed with H2O (3x20 mL), aqueous NaHCO3(2 x20 mL), and dried over Na2SO4. The solvent was removed ina rotary evaporator. The crude product was purified by flash chromatography(90:10 acetone/petroleum ether to give correspondingproduct. The purity and identity of the products were confirmed byGC-MS spectra, which were compared with the spectra in the NISTlibrary, and by 1H and 13C NMR spectroscopy. |
| 82% |
With potassium carbonate In water; chlorobenzene at 140℃; for 12h; Sealed tube; |
|
Reference：
[1]Nguyen, Linh Ho Thuy; Nguyen, Trang Thi Thu; Tran, Phuong Hoang; Kawazoe, Yoshiyuki; Le, Hung Minh; Doan, Tan Le Hoang
[Journal of Catalysis, 2019, vol. 374, p. 110 - 117]
[2]Wang, Lei; Ren, Xinyi; Yu, Jintao; Jiang, Yan; Cheng, Jiang
[Journal of Organic Chemistry, 2013, vol. 78, # 23, p. 12076 - 12081]
- 6
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[ 273-53-0 ]
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[ 1765-93-1 ]
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[ 397-54-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 87% |
With potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 10h; Green chemistry; |
2.5 General Method for C-H Arylation of Benzoxazole with Aryl Boronic Acids
General procedure: A mixture of benzoxazole (1mmol), aryl boronic acid(1 mmol), K2CO3(2mmol) and MNPFemBenzNHCNi complex (7) (100mg) in xylene (5mL) was stirred at100°C. The progress of reaction was monitored by TLC.After completion of reaction, 7 was separated by usingexternal magnet. Evaporation of solvent in vaccuo followedby column chromatography over silica gel using petroleumether/ethyl acetate aforded pure products. The productswere identified by FT-IR, 1H NMR, 13C NMR and mass |
|
With [2,2]bipyridinyl; potassium phosphate; [(nickel(II))2(1,4 dicarboxybenzene)2(1,4-diaza-bicyclo[2.2.2]octane)] In N,N-dimethyl acetamide at 100℃; for 3h; |
|
Reference：
[1]Naikwade, Altafhusen; Jagadale, Megha; Kale, Dolly; Gajare, Shivanand; Rashinkar, Gajanan
[Catalysis Letters, 2018, vol. 148, # 10, p. 3178 - 3192]
[2]Phan, Nam T. S.; Nguyen, Chung K.; Nguyen, Tung T.; Truong, Thanh
[Catalysis science and technology, 2014, vol. 4, # 2, p. 369 - 377]
- 7
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[ 7292-73-1 ]
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[ 88-75-5 ]
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[ 397-54-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 89% |
With potassium carbonate; In dimethyl sulfoxide; at 130℃; for 15h;Schlenk technique; Sealed tube; |
In a clean dry 10 ml Schlenk reaction tube, are sequentially added ortho-nitro phenol 35 mg, the fluorobenzene gly 113 mg, potassium carbonate 80 mg, in order to 1 ml of dimethyl sulfoxide as solvent, the reaction tube seal, in 130 C reaction under 15 hours. After the reaction, the reaction mixture directly by rotating the evaporimeter turns on lathe does, then the volume ratio of 35:1 of petroleum ether and ethyl acetate as the eluant, by separating by silica gel column, to obtain 47 mg of white solid, yield 89%. |
- 8
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[ 533-58-4 ]
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[ 456-14-4 ]
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[ 397-54-6 ]
- 9
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[ 95-56-7 ]
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[ 456-14-4 ]
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[ 397-54-6 ]
- 10
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[ 3834-66-0 ]
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[ 95-55-6 ]
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[ 397-54-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 58.1% |
With sodium hydroxide In o-xylene at 120℃; for 12h; |
Example of specific preparation method 2
0.15 mmol of 2-aminophenol, 0.2 mmol4-Fluorobibenzoyl, 0.4 mmol of sodium hydroxide (base) and 1.0 ml of o-xylene were mixed together at 120 ° C for 12 hours. After the reaction, it is extracted with an organic solvent, dried, filtered, concentrated, and purified by column chromatography to obtain2- (4-fluorophenyl) -benzoxazole with a yield of 58.1%. |
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