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[ CAS No. 24410-59-1 ]

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2D
Chemical Structure| 24410-59-1
Chemical Structure| 24410-59-1
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Product Details of [ 24410-59-1 ]

CAS No. :24410-59-1MDL No. :MFCD08236757
Formula : C8H5FO Boiling Point : 171.7°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :136.12Pubchem ID :11788322
Synonyms :

Computed Properties of [ 24410-59-1 ]

TPSA : 13.1 H-Bond Acceptor Count : 2
XLogP3 : 2.4 H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 24410-59-1 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 24410-59-1 ]

  • Upstream synthesis route of [ 24410-59-1 ]
  • Downstream synthetic route of [ 24410-59-1 ]

[ 24410-59-1 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 59769-37-8 ]
  • [ 24410-59-1 ]
YieldReaction ConditionsOperation in experiment
67% for 1.50 h; Reflux General procedure: A 25 mL round-bottomed flask was charged with 2-aryloxyacetaldehyde diethyl acetals (1 mmol), Sn-b (0.1 g), andtrifluorotoluene (10 mL). The mixture was stirred under refluxingcondition and monitored by GC. Upon completion, the mixture wascooled to room temperature, and the catalyst Sn-b was filtrate off.The filter cake was washed with trifluorotoluene (10 mL3). Thecombined filtratewas concentrated under vacuum. The residuewaspurified by flash column chromatography on SiO2 (petroleumether/ethyl acetate) to afford the desired 2,3-unsubstituted benzo[b]furans.
45% With PPA In benzene for 2.50 h; Heating / reflux To a mixture of benzene (200 ml) containing polyphosphoric acid (7.9 g, 0.035 mol) was added 2-(4-fluoro-phenoxy)-acetaldehyde diethyl acetal (8 g, 0.035 mol). The mixture was stirred vigorously while being heated to reflux for 2.5 hours. The reaction mixture was cooled to room temperature and decanted from the polyphosphoric acid. The solvent was removed under vacuum. Chromatography (5percent ethyl acetate-hexanes) afforded 3.4 g (45percent) of product as a clear oil: 1H NMR (CDCl3) δ 6.74 (dd, 1H, J = 2.0, 0.6 Hz), 7.01 (td, 1H, J = 9, 2.7 Hz), 7.25 (dd, 1H, J = 8.4, 2.7 Hz), 7.43 ( dd, 1H, J = 9, 3.9 Hz), 7.65 (d, 1H, J = 1.8 Hz).
Reference: [1] Tetrahedron, 2015, vol. 71, # 29, p. 4835 - 4841
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 15, p. 3823 - 3842
[3] Patent: EP1147083, 2004, B1. Location in patent: Page 35
[4] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[5] European Journal of Organic Chemistry, 2016, vol. 2016, # 13, p. 2268 - 2273
[6] Journal of Medicinal Chemistry, 2004, vol. 47, # 7, p. 1609 - 1612
[7] Patent: EP1380576, 2004, A1. Location in patent: Page 66
[8] Patent: WO2011/99010, 2011, A1. Location in patent: Page/Page column 38
[9] Patent: US2012/225863, 2012, A1. Location in patent: Page/Page column 17
[10] Patent: WO2012/119046, 2012, A2. Location in patent: Page/Page column 65-66
[11] New Journal of Chemistry, 2016, vol. 40, # 8, p. 6564 - 6567
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  • [ 371-41-5 ]
  • [ 24410-59-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 15, p. 3823 - 3842
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 7, p. 1609 - 1612
[3] Patent: US2012/225863, 2012, A1
[4] Patent: WO2012/119046, 2012, A2
[5] Patent: WO2015/42397, 2015, A1
[6] Tetrahedron, 2015, vol. 71, # 29, p. 4835 - 4841
[7] European Journal of Organic Chemistry, 2016, vol. 2016, # 13, p. 2268 - 2273
[8] New Journal of Chemistry, 2016, vol. 40, # 8, p. 6564 - 6567
[9] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
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