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CAS No. : | 21190-88-5 | MDL No. : | MFCD04116913 |
Formula : | C8H8BrNO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | OONBOXSIWCBAHZ-UHFFFAOYSA-N |
M.W : | 230.06 | Pubchem ID : | 2758810 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
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 dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; caesium fluoride; In 1,2-dimethoxyethane; at 80℃; for 4.5h;Schlenk technique; Inert atmosphere; | General procedure: A Schlenk tube was dried under vacuum, filled with nitrogen and charged consecutively with 1.00 eq bromine substrate, 1.00 eq boronic acid, 2.10 eq CsF, 0.05 eq PdCl2(dppf)*DCM and anhydrous DME (2 mL/0.15 mmol bromoarene). The suspension was degassed by vacuum/N2 cycles and stirred at 80 C. As TLC analysis or GC-MS analysis indicated full conversion of the starting material, the reaction mixture was cooled to rt and filtered through a pad of celite, which was rinsed with EtOAc and/or DCM. The solvent from the filtrate was removed under reduced pressure and final purification by column chromatography or silica gel filtration yielded the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride; In 1,2-dimethoxyethane; at 80℃;Schlenk technique; | General procedure: A Schlenk tube was dried under vacuum and charged with 1 0 eq halogenated substrate, 1.1 eq boronic acid, 5 mol% PdCb(dppf), 2.1 eq CsF, and anhydrous DME (~5 mL/100 mg halogenated substrate). The mixture was degassed via three cycles of vacuum/inert gas and was stirred at 80 C (oil-bath) overnight, after which time the reaction mixture was cooled to rt and optionally filtered through a pad of silica get or cotton. Subsequently, the solvent was removed under reduced pressure and final purification via column chromatography yielded the pure product. Reaction control was performed via TLC analysis and/or GC-MS analysis |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; In 1,2-dimethoxyethane; at 80℃;Schlenk technique; Inert atmosphere; | General procedure: A Schlenk tube was dried under vacuum and charged with 1.0 eq halogenated substrate, 1.1 eq boronic acid, 5 mol% PdCh(dppf), 2.1 eq CsF, and anhydrous DME (~5 mL/100 g halogenated substrate). The mixture was degassed by three cycles of vacuum/inert gas and was stirred at 80 C (oil-bath) overnight, after which time additional 0.3 eq boronic acid and 3 mol% PdCI2(dppf) were added. Subsequently, the reaction mixture was stirred at 80 C (oil-bath) overnight and was then cooled to rt and optionally filtered through a pad of silica gel or cotton. After solvent removal under reduced pressure, the crude product was purified via column chromatography. Reaction control was performed via TLC analysis and/or GC-MS analysis. |
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