HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 715922Generated: October 30, 2026
1,4-Dibromobenzene → tert-Butyl N-[(3R)-1-(4-bromophenyl)-5-oxopyrrolidin-3-yl]carbamate
https://huagongshe.com/reaction/715922
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,4-Dibromobenzene | HCID 7804 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | tert-Butyl [(3R)-5-oxopyrrolidin-3-yl]carbamate | HCID 71301758 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | tert-Butyl N-[(3R)-1-(4-bromophenyl)-5-oxopyrrolidin-3-yl]carbamate | HCID 117893470 | 13.5% |
Reaction Steps
1,4-Dioxane (8 ml) was added to 1,4-dibromobenzene (176 mg), t-butyl N-[(3R)-5-oxopyrrolidin-3-yl]carbamate (100 mg), tris(dibenzylideneacetone)dipalladium(0) (23 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (29 mg), and cesium carbonate (244 mg), and the mixture was stirred at 90° C. for 1 hour under an argon atmosphere and then further heated to reflux for 1 hour. Dichloromethane and water were added to the reaction solution to separate the aqueous and organic layers. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain the title compound (24 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09187489B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-47fa6811a9804c93a19622c178700d70 |
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| Source note | uspto-grants-2015_11 |
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