Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | (4-Methoxyphenyl)boronic acid | HCID 201262 | — |
| Reactant | HCID 70987382 | HCID 70987382 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86088095 | HCID 86088095 | 7% |
Reaction Steps
After palladium acetate (II) (37 mg, 0.16 mmol), tri-o-tolylphosphine (100 mg, 0.327 mmol) and a 2N aqueous sodium carbonate solution (2.5 ml) were added to a solution of methyl (3-iodo-2-methylphenyl)acetate (950 mg, 3.27 mmol) obtained in Example (33-1) and 4-methoxyphenylboronic acid (498 mg, 3.27 mmol) in N,N-dimethylformamide (8 ml), the mixture was stirred at 80° C. for 5 hours. After the reaction mixture was diluted with ethyl acetate and water, the insolubles were removed by filtration through Celite. After the obtained filtrate was extracted with ethyl acetate, the organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=9/1) to give methyl (4′-methoxy-2-methyl-1,1′-biphenyl-3-yl)acetate as a yellow powder (59 mg, yield: 7%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07923573B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-4f69d398f0c3484c9563bcae3d399bd0 |
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| Source note | uspto-grants-2011_04 |
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