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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2374238Generated: November 1, 2026

Triphenylarsine → 4-Methanesulfonyl-biphenyl-2-carboxylic acid methyl ester

https://huagongshe.com/reaction/2374238

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriphenylarsineHCID 11773—
ReactantTributylphenyltinHCID 607632—
ReactantMethyl 2-iodo-5-(methylsulfonyl)benzoateHCID 59853752—
CatalystCopper iodideHCID 83717—
CatalystTris(dibenzylideneacetone) dipalladiumHCID 9832798—
SolventDimethylformamideHCID 6228—
Product4-Methanesulfonyl-biphenyl-2-carboxylic acid methyl esterHCID 5775321799.5%

Reaction Conditions

Temperature90 °C

Reaction Steps

A mixture of 2-Iodo-5-methanesulfonyl-benzoic acid methyl ester (1.20 g, 3.53 mmol), Phenyltri-n-butyltin (1.27 ml, 3.88 mmol), Tris(dibenzylideneacetone) dipalladium(0) (226 mg, 0.25 mmol), Triphenylarsine (108 mg, 0.35 mmol) and Copper iodide (309 mg, 1.62 mmol) in N,N-Dimethylformamide (30 ml) was heated at 90° C. for 16 hours. The mixture was cooled to room temperature and concentrated in vacuo. The residue was chromatographed over SiO2 (ethyl acetate/heptane gradient) to provide the title compound (1.02 g, 99%) as an off-white crystalline solid. MS (ISP): 291.0 MH+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07462617B2
Source datasetuspto-grants-2008_12
ORD IDord-fcdd4c2aacd148789b1155dc66dd8937
Source noteuspto-grants-2008_12