Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | 4-Bromo-2-(dimethylamino)benzaldehyde | HCID 43364655 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | N,N-Dimethylformamide--water (1/1) | HCID 21962138 | — |
| Product | HCID 86639497 | HCID 86639497 | 91.2% |
Reaction Steps
To a suspension of 4-bromo-2-dimethylaminobenzaldehyde (250 mg, 1.10 mmol), sodium carbonate (140 mg, 1.32 mmol), and phenylboronic acid (210 mg, 1.65 mmol) in 2.2 mL of N,N-dimethylformamide/water (2:1) was added palladium acetate (13 mg, 58 μmol) under nitrogen. After being stirred at 100° C. overnight, the reaction mixture was filtered. The filtrate was diluted with ethyl acetate, and the solution was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 80/20) to obtain the title compound as a yellow oil (226 mg, 91%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08962674B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-1bc4f157239643e29eb7fca0cad197a3 |
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| Source note | uspto-grants-2015_02 |
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