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CAS No. : | 7311-63-9 | MDL No. : | MFCD00079725 |
Formula : | C5H3BrO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | COWZPSUDTMGBAT-UHFFFAOYSA-N |
M.W : | 207.05 | Pubchem ID : | 349115 |
Synonyms : |
|
Chemical Name : | 5-Bromothiophene-2-carboxylic acid |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
81% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; for 10h;Inert atmosphere; Reflux; | Potassium carbonate (0.667 g, 4.830 mmol) and <strong>[216019-28-2](3-isopropylphenyl)boronic acid</strong> (0.3960 g, 2.415 mmol) were added to a 20 mL scintillation vial with DI water (1 mL) and absolute EtOH (8 mL). The vial was purged with argon. Next 5-bromo-2-thiophenecarboxylic acid (0.500 g, 2.415 mmol) was added, followed by Pd(PPh3)4 (0.139 g, 0.1207 mmol). The vial was purged with argon again then heated at reflux for 10 h. The reaction was cooled, acidified with 10% HCl, and extracted with EtOAc three times. The combined organic layers were washed with sat. aq. NaHCC three times. The basic aqueous layer was then acidified with 10% HCl, resulting in precipitation of the product. The precipitate was removed by gravity filtration and dried overnight open to the atmosphere. Product was isolated as a pale yellow solid in 81% yield (0.4829 g). NMR (400 MHz, DMSO-de) delta 13.08 (broad s, 1H), 7.72 (d, J = 3.9 Hz, 1H), 7.60-7.57 (m, 2H), 7.54 (d, J= 7.8 Hz, 1H), 7.38 (t, J = 7.7 Hz, 1H), 7.29 (d, J = 7.7 Hz, 1H), 2.96 (sept, J = 6.9 Hz, 1H), 1.25 (d, J = 6.9 Hz, 6H). |
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