Cesium carbonate → 1-Dimethylphosphoryl-3-nitrobenzene

HRID 409956

反応式

HRID 409956 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 1902781-Dimethylphosphoryl-3-nitrobenzene収率 79.5%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

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 cabonate (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).

後処理

  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)

出典と根拠

ORDレコード
ord-dec26ec910c14b168511843357aa73d6
出典データセット
uspto-grants-2014_06
特許番号
US08759522B2

関連ノート

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