Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Acetyl-5-bromothiophene | HCID 79335 | — |
| Reactant | 4-Hydroxyphenylboronic acid | HCID 2734360 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 21931579 | HCID 21931579 | — |
Reaction Steps
A flame-dried test tube under N2 was charged with 1-(5-bromothiophen-2-yl)ethanone (250 mg, 1.22 mmol), p-hydroxyphenylboronic acid (1.2 equiv, 1.40 mmol, 202 mg), and 2.0 mL 1,4-dioxane. To the yellow solution, tetrakistriphenylphosphinepalladium(0) (6 mol %, 0.0731 mmol, 84 mg) and 2 M aqueous sodium carbonate (2.0 equiv, 2.44 mmol, 2.0 mL) were added. The yellow mixture was heated to 100° C. for 18 h. The resulting yellow-brown mixture was cooled to rt, adsorbed onto Celite in vacuo, and purified by silica gel chromatography to afford the desired product as an analytically pure yellow solid (51 mg, 19% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08664255B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-b7c792fb287b43b4bdf635222b91525b |
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| Source note | uspto-grants-2014_03 |
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