Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Formylphenylboronic acid | HCID 2734356 | — |
| Reactant | HCID 23157610 | HCID 23157610 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 23157353 | HCID 23157353 | 28% |
Reaction Steps
A mixture of 2-bromo-5-(2-ethoxyethoxy)-1,3,4-trimethylbenzene (1.16 g, 4.04 mmol), 3-formylphenylboronic acid (0.67 g, 4.44 mmol), tetrakis(triphenylphosphine)palladium(0) (0.23 g, 0.20 mmol), cesium carbonate (3.2 g, 9.7 mmol), water (4.8 mL) and 1,2-dimethoxyethane (15 mL) was stirred under a nitrogen atmosphere at 90° C. for 64 hr. The reaction mixture was diluted with ethyl acetate, washed successively with water and saturated brine, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1) to give the title compound (0.35 g, yield 28%) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07786165B2 |
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| Source dataset | uspto-grants-2010_08 |
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| ORD ID | ord-daf6ee35fac6420bad4768e825d82336 |
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| Source note | uspto-grants-2010_08 |
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