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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

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,4-DibromobenzeneHCID 7804—
ReactantCesium carbonateHCID 10796—
Reactant1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 636044—
Reactanttert-Butyl [(3R)-5-oxopyrrolidin-3-yl]carbamateHCID 71301758—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventWaterHCID 962—
SolventDichloromethaneHCID 6344—
Solvent1,4-DioxaneHCID 31275—
Producttert-Butyl N-[(3R)-1-(4-bromophenyl)-5-oxopyrrolidin-3-yl]carbamateHCID 11789347013.5%

Reaction Conditions

Temperature90 °C

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09187489B2
Source datasetuspto-grants-2015_11
ORD IDord-47fa6811a9804c93a19622c178700d70
Source noteuspto-grants-2015_11