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Chemical Structure| 7519-91-7 Chemical Structure| 7519-91-7

Structure of 7519-91-7

Chemical Structure| 7519-91-7

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Product Details of [ 7519-91-7 ]

CAS No. :7519-91-7
Formula : C18H12B3Cl3O3
M.W : 415.08
SMILES Code : ClC1=CC=C(B2OB(C3=CC=C(Cl)C=C3)OB(C4=CC=C(Cl)C=C4)O2)C=C1

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Application In Synthesis of [ 7519-91-7 ]

* 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 [ 7519-91-7 ]
  • Downstream synthetic route of [ 7519-91-7 ]

[ 7519-91-7 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 7519-91-7 ]
  • [ 105-53-3 ]
  • [ 19677-37-3 ]
YieldReaction ConditionsOperation in experiment
77% With cesium acetate; copper(II) bis(trifluoromethanesulfonate); triethylamine In 1,2-dichloro-ethane at 30℃; for 48 h; Sealed tube General procedure: In an atmosphere controlled glovebox, Cu(OTf)2 (398 mg, 1.10 mmol, 2.20 equiv.), arylboroxine (0.330 mmol, 0.670 equiv.), and CsOAc (106 mg, 0.550 mmol, 1.10 equiv.) were added sequentially to a 2 dram vial charged with a stir bar. The sp3-carbon nucleophile (0.500 mmol, 1.00 equiv.) and triethylamine (0.210 mL, 1.50 mmol, 3.00 equiv.) were added as a solution in anhydrous 1,2-DCE (1.20 mL). Additional 1,2-DCE (2×0.5 mL) was used to quantitatively transfer the solution to the reaction mixture. The vial was sealed with a PTFE-lined cap and stirred outside the glovebox at 30° C. Reaction progress was generally monitored by GC-FID using n-dodecane as an internal standard. Unless otherwise noted, reactions were quenched after 36-48 hours, when >95percent conversion of sp3-carbon nucleophile was reached. The reaction was quenched with 5 mL of brine and extracted with EtOAc (4×10 mL). The organic layer was then washed with 5 mL brine and dried with Na2SO4, and the solvent was removed by vacuum. The crude residue was purified by flash silica gel chromatography. Note: the order of addition of reagents is important for achieving optimal yields.
References: [1] Angewandte Chemie, International Edition, 2016, vol. 55, # 5, p. 1894 - 1898.
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 5, p. 1894 - 1898[3] Angew. Chem., 2016, vol. 128, # 5, p. 1926 - 1930,5.
[4] Patent: US2018/186721, 2018, A1, . Location in patent: Paragraph 0142; 0143; 0176.
 

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