Cesium carbonate → 1-Dimethylphosphoryl-3-nitrobenzene

HRID 1026797노트

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HRID 1026797 반응식
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[CH3:11][PH:12](=[O:14])[CH3:13].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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]>[CH3:11][P:12]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1)([CH3:13])=[O:14]

참가 물질

7

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HCID 10796Cesium carbonateHCID 125741-Iodo-3-nitrobenzeneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 178503022methylphosphonoylmethane

생성물 1

HCID 1902781-Dimethylphosphoryl-3-nitrobenzene수율 79.5%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

To a solution of 1-iodo-3-nitrobenzene (2.4 g, 9.6 mmol) in dry 1,4-dioxane (24 ml) in a pressure bottle under nitrogen at room temperature was added dimethylphosphine oxide [WO 2005/009348] (1.5 g, 19.2 mmol), Pd2(dba)3 (0.44 g, 0.48 mmol), Xantphos (0.56 g, 0.96 mmol) and cesium carbonate (4.38 g, 13.5 mmol). The mixture was degassed by bubbling nitrogen into the solution for 10 min. The pressure bottle was closed and heated at 90° C. for 3 h. The solvent was removed under reduced pressure and the residue was purified via Biotage (linear gradient 0-20%, methanol/ethyl acetate; 25M column) to afford title compound 286 as a brown solid (1.52 g, 7.63 mmol, 79%). MS (m/z): 200.1 (M+H).

후처리

  1. customThe mixture was degassed
  2. customby bubbling nitrogen into the solution for 10 min
  3. customThe pressure bottle was closed
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified via Biotage (linear gradient 0-20%, methanol/ethyl acetate; 25M column)

출처 및 근거

ORD 기록
ord-b118d6edd9b34f428f2ef93cd4c4f790
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729268B2

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