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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1852910Generated: October 31, 2026

1,3-Dibromobenzene → HCID 71138417, compound

https://huagongshe.com/reaction/1852910

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,3-DibromobenzeneHCID 7927—
ReactantEthyl 4-piperidinecarboxylateHCID 70770—
ReactantBinap, (A+-)-HCID 634876—
ReactantSodium t-butoxideHCID 23676156—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
SolventEthyl AcetateHCID 8857—
ProductHCID 71138417HCID 7113841742.7%

Reaction Conditions

Temperature80 °C

Reaction Steps

To a solution of 1,3-dibromobenzene (10 g, 42 mmol) in toluene (424 mL), were added ethyl isonipecotate (6.5 mL, 42 mmol), rac-BINAP (2.0 g, 3.2 mmol), NaOtBu (4.9 g, 51 mmol) and Pd2(dba)3 (0.97 g, 1.1 mmol). The mixture was heated at 80° C. for 4 h and diluted with water and ethyl acetate and separated. The organic phase was dried over unhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate 10:0 to 9:1) to give the titled compound (5.6 g, 42%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08962619B2
Source datasetuspto-grants-2015_02
ORD IDord-260a500110bf437cbec56258203b414c
Source noteuspto-grants-2015_02