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CAS No. : | 154230-29-2 | MDL No. : | MFCD02093767 |
Formula : | C8H8BClO2 | Boiling Point : | - |
Linear Structure Formula : | ClC6H4CHCHB(OH)2 | InChI Key : | HWSDRAPTZRYXHN-AATRIKPKSA-N |
M.W : | 182.41 | Pubchem ID : | 642694 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54 - 55% | With potassium phosphate; triphenylphosphine;palladium diacetate; In acetonitrile; at 94℃; for 32h; | To a 40-mL scintillation vial containing trans-2-(4-chlorophenyl)vinylboronic acid (0.42 g, 2.30 mmol), <strong>[18791-78-1]3-bromo-4-formylthiophene</strong> (0.40 g, 2.09 mmol), K3PO4 (0.490 g, 2.30 mmol), TPP (22 mg, 0.08 mmol, 4 mol %), Pd(OAc)2 (4.7 mg, 0.02 mmol, 1 mol %) and a stir-bar, was added acetonitrile (2.5 mL). The vial was purged with N2, capped tightly and heated at 94 C. (aluminum multi-reaction block) while vigorously stirred for 32 h. The reaction was diluted with water and extracted with EtOAc (3*50 mL). The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Purification by flash chromatography (Isco CombiFlash) 0-10% EtOAc in heptane afforded the desired 4-[2-(4-chlorophenyl)-vinyl]-thiophene-3-carbaldehyde (285 mg, 54%). 1H NMR (400 MHz, CDCl3) delta ppm 6.99 (d, J=16.38 Hz, 1H), 7.31-7.36 (m, 2H), 7.45-7.49 (m, 2H), 7.50 (d, J=3.20 Hz, 1H), 7.76 (dd, J=16.34, 0.78 Hz, 1H), 8.13 (d, J=3.20 Hz, 1H), 10.07 (d, J=0.82 Hz, 1H). |
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