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

HRID 225718

반응식

HRID 225718 반응식
[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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[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]

참가 물질

7

반응물 3

HCID 11773TriphenylarsineHCID 607632TributylphenyltinHCID 59853752Methyl 2-iodo-5-(methylsulfonyl)benzoate

생성물 1

HCID 577532174-Methanesulfonyl-biphenyl-2-carboxylic acid methyl ester수율 99%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

A mixture of 3.53 mmol 2-Iodo-5-methanesulfonyl-benzoic acid methyl ester, 3.88 mmol Phenyltri-n-butyltin, 0.25 mmol Tris(dibenzylideneacetone)dipalladium(0), 0.35 mmol Triphenylarsine and 1.62 mmol Copper iodide 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 (99%) as an off-white crystalline solid. MS (m/e): 291.0 (MH+, 100%)

후처리

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

출처 및 근거

ORD 기록
ord-080b43447f2e4e1ea5a6295673c01f4d
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557114B2

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