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

HRID 2374238Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1I.[C:16]1([Sn](CCCC)(CCCC)CCCC)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Cu](I)I>[CH3:1][O:2][C:3]([C:4]1[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:6][CH:7]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:9]=1)=[O:15]

Participants

Conditions

Temperature: 90 °C

Procedure

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+.

Workup

temperatureThe mixture was cooled to room temperature
concentrationconcentrated in vacuo
customThe residue was chromatographed over SiO2 (ethyl acetate/heptane gradient)

Sources & evidence

ORD record: ord-fcdd4c2aacd148789b1155dc66dd8937
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462617B2

Reaction notes

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