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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1914030Generated: November 1, 2026

1,3-Dibromobenzene → HCID 71138719, compound

https://huagongshe.com/reaction/1914030

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,3-DibromobenzeneHCID 7927—
ReactantBinap, (A+-)-HCID 634876—
ReactantThiomorpholine 1,1-dioxideHCID 6484228—
ReactantSodium t-butoxideHCID 23676156—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventTolueneHCID 1140—
SolventDichloromethaneHCID 6344—
ProductHCID 71138719HCID 7113871948.4%

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of 1,3-dibromobenzene (242 μL, 2.00 mmol), thiomorpholine 1,1-dioxide (270 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 11 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=90:10→80:20→75:25) to afford desired product (281 mg, 48.4%) as pale yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08609688B2
Source datasetuspto-grants-2013_12
ORD IDord-54e12e1baf7c45309f2dd31a9fc35feb
Source noteuspto-grants-2013_12