Cesium carbonate → 4-Methoxy-2-nitro-biphenyl

HRID 1518633ノート

反応式

HRID 1518633 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13]1(OB(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 78412Phenyl dihydrogen orthoborateHCID 792884-Bromo-3-nitroanisole

生成物 1

HCID 114019374-Methoxy-2-nitro-biphenyl収率 81.1%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

1-Bromo-4-methoxy-2-nitrobenzene (2.32 g, 10 mmol) was dissolved in 1,4-dioxane (30 mL) and, thereto, were added phenyl boric acid (2.44 g, 20 mmol), cesium carbonate (26 g, 80 mmol), 1,1-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (0.82 g, 1 mmol), and purified water (12 mL). The reaction mixture was stirred under a nitrogen flow at 80° C. for 18 hours. The reaction solution was filtered through celite, alumina, and Florisil, and, thereafter, extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography to obtain 4-methoxy-2-nitro-1-phenylbenzene (1.86 g).

後処理

  1. custompurified water (12 mL)
  2. filtrationThe reaction solution was filtered through celite, alumina, and Florisil
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-44fedd1f22a34adb8e981105e0614b93
出典データセット
uspto-grants-2015_07
特許番号
US09072734B2

反応ノート

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