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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1914039Generated: October 29, 2026

1,3-Dibromobenzene → HCID 71138690, compound

https://huagongshe.com/reaction/1914039

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,3-DibromobenzeneHCID 7927—
ReactantBinap, (A+-)-HCID 634876—
Reactant8-Oxa-3-azabicyclo[3.2.1]octaneHCID 12069231—
ReactantSodium t-butoxideHCID 23676156—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventTolueneHCID 1140—
SolventDichloromethaneHCID 6344—
ProductHCID 71138690HCID 7113869067.3%

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of 1,3-dibromobenzene (242 μL, 2.00 mmol), 8-oxa-3-azabicyclo[3.2.1]octane (226 mg, 2.00 mmol), Pd2(dba)3 (45.8 mg, 0.0500 mmol), rac-BINAP (96.3 mg, 0.150 mmol) and NaOtBu (231 mg, 2.40 mmol) in toluene was heated at 80° C. for 13 hours under nitrogen. After cooling to room temperature, the mixture was diluted with DCM and filtered through a Celite pad. The combined filtrate and washings were concentrated. The residue was purified by silica gel column chromatography (EtOAc/hexane=9:1) to afford desired product (361 mg, 67.3%) as colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08609688B2
Source datasetuspto-grants-2013_12
ORD IDord-2d4c154df52341cfabc3687646c7f675
Source noteuspto-grants-2013_12