Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (2H-1,3-benzodioxol-5-yl)boronic acid | HCID 2734371 | — |
| Reactant | Methyl 2-(benzamido)-4-bromobenzoate | HCID 57879335 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 57879355 | HCID 57879355 | 56.8% |
Reaction Steps
52 mg of 3,4-methylenedioxyphenylboronic acid, 55 mg of sodium carbonate and 30 mg of polymer supported bis(acetato)triphenylphosphine palladium(II) were added to 2.5 mL of N,N-dimethylacetamide solution containing 70 mg of methyl 2-(benzamido)-4-bromobenzoate, and stirred at 90° C. for 22 hours. After the reaction mixture was cooled to room temperature, insoluble were removed by filtration and ethyl acetate and 1.2 mol/L hydrochloric acid were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 1.0 mol/L hydrochloric acid and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. 1.0 mL of 1.0 mol/L aqueous sodium hydroxide and 2.0 mL of ethanol were added to the obtained residue and stirred at room temperature for 1 hour. 0.6 mol/L hydrochloric acid was added to the reaction mixture and a solid substance was separated by filtration to obtain 43 mg of 2-(benzamido)-4-(benzo[1,3]dioxol-5-yl)benzoic acid as white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07999132B2 |
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| Source dataset | uspto-grants-2011_08 |
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| ORD ID | ord-0df3703413184a55aebaa12c81cbc49a |
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| Source note | uspto-grants-2011_08 |
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