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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 71069Generated: October 26, 2026

Toluene → HCID 59489238, compound

https://huagongshe.com/reaction/71069

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
Reactant2,8-DibromodibenzothiopheneHCID 631120—
Reactant2-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 11269872—
Reactant4,4,5,5-TetraMethyl-2-(3-triphenylen-2-yl-phenyl)-[1,3,2]dioxaborolaneHCID 58769449—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventWaterHCID 962—
ProductHCID 59489238HCID 5948923894%

Reaction Steps

2.25 g (6.3 mmol) of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane, 0.92 g (2.7 mmol) of 2,8-dibromodibenzothiophene, 0.12 g (0.14 mmol) of Pd2(dba)3, 0.22 g (0.53 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, 3.4 g (16.0 mmol) of K3PO4100, mL of toluene and 10 mL of water were charged in a 250 mL round bottom flask. The reaction mixture was purged with nitrogen for 20 min and then heated up to reflux for overnight with stirring. The reaction mixture was cooled and filtered. The white solid was washed with methanol 3 times (3×100 mL) and methylene chloride (2×100 mL). 1.6 g of (94% yield) solid was obtained as the product which was further purified by recrystallization with toluene and sublimation. The product was confirmed by solid probe MS.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08822708B2
Source datasetuspto-grants-2014_09
ORD IDord-5da14525b29e488182d2a090fd4f6ed0
Source noteuspto-grants-2014_09