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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 488515Generated: October 27, 2026

Cesium carbonate → 2-{4-[2-(3,4-Dimethyl-phenyl)-ethyl]phenylamino)-5-nitrobenzoic acid methyl ester

https://huagongshe.com/reaction/488515

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
ReactantMethyl 2-Bromo-5-nitrobenzoateHCID 245494—
Reactant4-[2-(3,4-Dimethylphenyl)ethyl]-benzenamineHCID 14555209—
CatalystPalladiumHCID 23938—
CatalystDi-p-tolylphosphino-1,1'-binaphthylHCID 18398271—
SolventTolueneHCID 1140—
Product2-{4-[2-(3,4-Dimethyl-phenyl)-ethyl]phenylamino)-5-nitrobenzoic acid methyl esterHCID 5413991487.8%

Reaction Steps

The title compound was prepared from 4-[2-(3,4-dimethylphenyl)ethyl]-benzenamine (1.0 g, 4.43 mmol), 2-bromo-5-nitrobenzoic acid methyl ester (0.96 g, 3.69 mmol), cesium carbonate (1.68 g, 5.17 mmol), tris(dibenzylideneacetone-dipaladium(0) (101 mg, 0.11 mmol) and (S)-(2,2′-bis(di-p-tolylphosphino-1,1′-binaphthyl (98%, (S)-tol-BINAP) (113 mg, 0.17 mmol) (Ligand/Pd=1.5) in anhydrous toluene (32 mL) using the procedure described in Example 2, step C. This procedure yielded an yellow solid, 1.31 g (3.24 mmol, 73%) of the desired product. mp 115-117° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06972287B1
Source datasetuspto-grants-2005_12
ORD IDord-29762f8125c9414e9b2f781c10b073b5
Source noteuspto-grants-2005_12