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CAS No. : | 5570-18-3 | MDL No. : | MFCD01074645 |
Formula : | C6H8BNO2 | Boiling Point : | No data available |
Linear Structure Formula : | (C6H4)(NH2)B(OH)2 | InChI Key : | DIRRKLFMHQUJCM-UHFFFAOYSA-N |
M.W : | 136.94 | Pubchem ID : | 2773216 |
Synonyms : |
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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 |
---|---|---|
39% | With [Rh(OH)(cod)]2; surfactant TPGS-750-M; potassium carbonate; In water; at 20℃; for 24h;Green chemistry; | General procedure: In a 5 mL microwave vial containing alpha,beta-unsaturated ethyl ester (100mg, 1.00equiv), boronic ester (2.00 equiv), potassium carbonate (2.00 equiv) and [RhOH(COD)]2 (0.05 equiv) was added 2% wt. TPGS-750-M solution in water (3 mL). The mixture was stirred vigorously at ambient temperature for the indicated time. The reaction mixture was then extracted with ethyl acetate. The organic phase was subsequently dried over MgSO4, filtrated and reduced under vacuum. The crude product was purified by column chromatography on silica (eluent: 0-10% methanol in dichloromethane) to yield the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl?)]palladium(II); In tetrahydrofuran; water; at 60℃; for 16h;Inert atmosphere; | Degassed THF (30 ml) and water (6 ml) were added to a 250 ml flask containing <strong>[18442-22-3]7-bromochroman-4-one</strong> (5 g, 22 mmol), 2-(aminophenyl)boronic acid (3.02 g, 22 mmol), K3P04(9.35 g, 44 mmol), and chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl- 1,1 ?-biphenyl) [2-(2?-amino- 1,1 ?-biphenyl)jpalladium(II) (866 mg, 1.1 mmol). The mixture was placed under an argon atmosphere, and evacuated and purged with nitrogen three times. The reaction was heated at 60 C for 16 h, then cooled to room temperature and the solvent was evaporated under reduced pressure. The resulting crude product was diluted with water (50 ml), extracted with ethylacetate (x2), dried over anhydrous magnesium sulfate, filtered and concentrated under reducedpressure. The resulting residue was purified by column chromatography on silica (0-60%EtOAc/hexanes) to afford 7-(2-aminophenyl)chroman-4-one: MS ESI calcd. for C15H14N02 [M+ Hj 240, found 240. |
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