Dimethylformamide → 2-Nitro-5-(3-nitrophenoxy)pyridine

HRID 1874320

反応式

HRID 1874320 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[N:16][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[N+:18]([C:15]1[CH:14]=[CH:13][C:12]([O:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[CH:17][N:16]=1)([O-:20])=[O:19]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 111373-NitrophenolHCID 8176205-Bromo-2-nitropyridine

生成物 1

HCID 577491152-Nitro-5-(3-nitrophenoxy)pyridine収率 33%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

A mixture of 3-nitrophenol (7.76 g, 55.8 mmol), 5-bromo-2-nitropyridine (10.3 g, 50.7 mmol), cesium carbonate (24.8 g, 76.1 mmol) and N,N-dimethylformamide (150 mL) was stirred at 50° C. for 15 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (NH silica gel, hexane/ethyl acetate=100/0→0/100) to give the title compound (4.37 g, 33%) as a yellow solid.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography (NH silica gel, hexane/ethyl acetate=100/0→0/100)

出典と根拠

ORDレコード
ord-61c3a775f1bc4aebb58828d59309736e
出典データセット
uspto-grants-2012_11
特許番号
US08304557B2

関連ノート

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