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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 539456Generated: October 31, 2026

Toluene → 5-Methoxy-[1,1'-biphenyl]-3-carbonitrile

https://huagongshe.com/reaction/539456

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantPhenylboronic AcidHCID 66827—
Reactant3-Bromo-5-methoxybenzonitrileHCID 25067362—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Catalyst2-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 11269872—
SolventEthyl AcetateHCID 8857—
Product5-Methoxy-[1,1'-biphenyl]-3-carbonitrileHCID 7065447391.7%

Reaction Steps

3-bromo-5-methoxybenzonitrile (8.3 g, 39.1 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (S-Phos) (1.286 g, 3.13 mmol), phenylboronic acid (5.84 g, 47.0 mmol), Pd2(dba)3 and 200 mL toluene were charged in a flask and refluxed overnight. The reaction was cooled down and 200 mL of ethyl acetate was added. The crude mixture was run though a silica gel plug, and the product was confirmed by GC. After distillation under vacuum, 7.5 g of a white product was obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08871361B2
Source datasetuspto-grants-2014_10
ORD IDord-d498e7d55f294cc1931146d566d34271
Source noteuspto-grants-2014_10