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CAS No. : | 175883-63-3 | MDL No. : | MFCD04039010 |
Formula : | C7H8BClO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | YTJUYWRCAZWVSX-UHFFFAOYSA-N |
M.W : | 170.40 | Pubchem ID : | 3854610 |
Synonyms : |
|
Chemical Name : | 3-Chloro-4-methylphenylboronic Acid |
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 |
---|---|---|
84.0% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 1.5h;Inert atmosphere; | A 50-mL round-bottom flask was charged with 5-bromo-2-methoxy aniline(Alfa Aesar, 1.00 g, 4.95 mmol), 3-chloro-4-methylphenylboronic acid (Acros, 1.69 g, 9.90 mmol), 1,1 '-bis(diphenylphosphino)ferrocene palladium(II)dichloride dichloromethane adduct (0.81 g, 0.99 mmol), and purged with nitrogen. 1,4-Dioxane (37.1 ml) and an aqueous sodium carbonate solution (1.9 M, 12.4 mL) were introduced and the reaction mixture was warmed to 80 °C. After 90 min, the reaction mixture was allowed to cool to ambient temperature and diluted with aqueous HCI solution (1.0 M, 25 mL) and EtOAc (25 mL). The layers were separated and the aqueous layer extracted with additional EtOAc (2 x 25 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and purified by flash column chromatography (100-g silica gel Biotage column, eluent: gradient, 0 to 40percent EtOAc in heptane with DCM as a 5percent additive) to afford 3'-chloro-4-methoxy-4'-methyl-[l,l'-bipheny 1]-3-amine (1.03 g, 4.16 mmol, 84.0 percent yield) as a tan solid. |
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