Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Bromobenzene | HCID 7961 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | HCID 58504081 | HCID 58504081 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Product | HCID 58504041 | HCID 58504041 | 55.7% |
Reaction Steps
A flask was charged with the compound prepared in Example 302 (0.533 g), 1-bromobenzene (0.252 g), potassium tert-butoxide (0.252 g), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.056 mg), and bis(dibenzylideneacetone)palladium (0.037 g) and flushed with nitrogen gas. Toluene (30 mL) which was thoroughly purged with nitrogen gas was added and the reaction mixture heated at 105° C. for 18 hours. The reaction mixture was concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (eluant: 10% ethyl acetate/hexane) to furnish the title compound (0.365 g) with the following physical properties.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08809538B2 |
|---|
| Source dataset | uspto-grants-2014_08 |
|---|
| ORD ID | ord-3430b6e2ba7242c6aaf06b97e227c218 |
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| Source note | uspto-grants-2014_08 |
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