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Chemistry
Heterocyclic Building Blocks
Benzofurans
Ethyl 5-fluorobenzofuran-2-carboxylate
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Benzofurans
Fluorinated Building Blocks Esters

[ CAS No. 93849-31-1 ] {[proInfo.proName]}

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Chemical Structure| 93849-31-1
Chemical Structure| 93849-31-1
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Quality Control of [ 93849-31-1 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 93849-31-1 ]

CAS No. :93849-31-1 MDL No. :MFCD09038171
Formula : C11H9FO3 Boiling Point : -
Linear Structure Formula :- InChI Key :RBQUPHUYCPBKSF-UHFFFAOYSA-N
M.W : 208.19 Pubchem ID :11052832
Synonyms :

Safety of [ 93849-31-1 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 93849-31-1 ]

* 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 [ 93849-31-1 ]

[ 93849-31-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 93849-31-1 ]
  • [ 89197-62-6 ]
YieldReaction ConditionsOperation in experiment
87% With sodium hydroxide In methanol; water; N,N-dimethyl-formamide at 20℃;
With potassium hydroxide In ethanol for 0.75h; Heating; Yield given;
With sodium hydroxide In water; N,N-dimethyl-formamide at 60℃; for 0.5h; General procedure: To a solution of intermediates 3a-3q (1mmol) in 10ml DMF, 2.0mL of 20% sodium hydroxide solution was dropped at 60°C to carry out the ester hydrolysis reaction for 30min. Afterwards, the mixture was cooled to room temperature, and the PH value of the solution was adjusted to 2 using 10% hydrochloric acid, then the mixture was extracted with ethyl acetate. The organic phase was combined and condensed by vacuum concentration to afford the crude product, which was purified by recrystallization to give the designed compounds (4a-4q).
Stage #1: ethyl 5-fluoro-1H-benzofuran-2-carboxylate With water; sodium hydroxide In ethanol for 1h; Heating; Stage #2: With hydrogenchloride In ethanol; water

Reference： [1]Wang, Yuqiang; Li, Lianfa; Ye, Wenqing; Tian, Zhiming; Jiang, Wei; Wang, Hong; Wright, Susan C.; Larrick, James W. [Journal of Medicinal Chemistry, 2003, vol. 46, # 4, p. 634 - 637]
[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]Kong, Ling-Yi; Leng, Jia-Fu; Lian, Bao-Ping; Shao, Yu-Ying; Xia, Yuan-Zheng; Yin, Yong [European Journal of Medicinal Chemistry, 2020, vol. 190]
[4]Cao, Zhi-Ling; Liu, Shu-Hao; Liu, Wei-Wei; Liu, Xiu-Jian; Ren, Shu-Ting; Shi, Da-Hua; Wang, Lei; Wang, You-Xian; Wu, Yu-Ran [Heterocyclic Communications, 2019, vol. 25, # 1, p. 162 - 166]
  • 2
  • [ 174775-48-5 ]
  • [ 93849-31-1 ]
Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 634 - 637
  • 3
  • [ 93849-31-1 ]
  • [ 276235-91-7 ]
YieldReaction ConditionsOperation in experiment
84% With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.5h; 83.2 Step 2:
(5-fluorobenzofuran-2-yl)methanol. Step 2: (5-fluorobenzofuran-2-yl)methanol To an ice-cooling solution of ethyl 5-fluorobenzofuran-2-carboxylate (450 mg, 2.16 mmol) in THF (10 mL) was added AlH4Li (82 mg, 2.16 mmol). The resulted mixture was stirred at 0° C. for 0.5 h, and then the reaction was quenched by addition of NaSO4.10H2O. After filtration, the filter cake was washed with ethyl acetate, the filtrate was evaporated under vacuum. The residue was purified by prep-TLC (petroleum ether:ethyl acetate=5:1) to afford (5-fluorobenzofuran-2-yl)methanol (300 mg, yield: 84%) as colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.39 (dd, J=4.0, 8.8 Hz, 1H), 7.20-7.23 (m, 1H), 6.99-7.04 (m, 1H), 6.64 (s, 1H), 4.78 (s, 1H), 2.24 (s, 1H).
83% With diisobutylaluminium hydride In tetrahydrofuran at -60℃; for 2h; 56B mple 5 - (5-fluorobenzofuran-2-yl)methanol (B-156) To a solution of compound B-155 (6.0 g, 29 mmol) in tetrahydrofuran (60 mL) at - 60 °C was added dropwise diisobutylaluminium hydride (64 mL, 64 mmol). The resulting solution was stirred at -60 °C for 2 hours until TLC showed the reaction was complete. The reaction was quenched with saturated aqueous citric acid solution (50 mL) and extracted with dichloromethane (3 χ 50 mL). The combined organic phases were washed with brine, dried over sodium sulfate and concentrated in vacuo to give compound B-156 (4.0 g, 83% yield) as a white solid.
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.333333h;
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Schlenk technique;
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.333333h; 6.1 LiAlH4 (0.19 g, 5.0 mmol) was weighed into a flask, THF (20.0 mL) was added,After stirring at 0 ° C for 10 minutes, a compound represented by the formula 2-f (1.04 g, 5.0 mmol)After stirring at 0 ° C for 20 minutes, the reaction was quenched by the addition of H2O (5 mL), diluted with ethyl acetate,Filtered, washed with ethyl acetate, concentrated by rotary distillation and purified by silica gel column chromatography to give the product of formula 3-f.

Reference： [1]Current Patent Assignee: SHENZHEN LANGRUN INVESTMENT CO., LTD. - US2017/37038, 2017, A1 Location in patent: Paragraph 0384; 0387
[2]Current Patent Assignee: FORUM PHARMACEUTICALS INC - WO2015/66371, 2015, A1 Location in patent: Paragraph 00312-00313
[3]Location in patent: scheme or table Byun, Ji Hun; Kim, HyeYun; Kim, YoungSoo; Mook-Jung, Inhee; Kim, Dong Jin; Lee, Won Koo; Yoo, Kyung Ho [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5591 - 5593]
[4]Tian, Qingshan; Bai, Jing; Chen, Bin; Zhang, Guozhu [Organic Letters, 2016, vol. 18, # 8, p. 1828 - 1831]
[5]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Institute of Chemistry (in: CAS) - CN106588952, 2017, A Location in patent: Paragraph 0119; 0121-0122; 0124

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