4-Methoxybenzaldehyde → 1-(2-Chloro-2-nitrovinyl)-4-methoxybenzene

HRID 1926899ノート

反応式

HRID 1926899 の反応式
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.Br[CH2:12][N+:13]([O-:15])=[O:14].[Cl-:16].C[NH2+]C.[F-].[K+]>C1(C)C(C)=CC=CC=1.ClCCl.O>[Cl:16]/[C:12](/[N+:13]([O-:15])=[O:14])=[CH:7]\[C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

参加物

8

反応物 4

HCID 312444-MethoxybenzaldehydeHCID 68423BromonitromethaneHCID 522689Potassium FluorideHCID 12954980Dimethylazanium;chloride

生成物 1

HCID 58207481-(2-Chloro-2-nitrovinyl)-4-methoxybenzene

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒HCID 7237O-Xylene溶媒

実験手順

As in a procedure described in the literature [D. Dauzonne, Synthesis, 1990, 66-70], stir a mixture of 10.0 g (73.5 mmol) 4-methoxybenzaldehyde, 9.0 ml (13.5 g, 96.2 mmol) bromonitromethane, 53.9 g (661.0 mmol) dimethylammonium chloride and 0.6 g (1.0 mmol) potassium fluoride in 150 ml xylene on a water separator at 160° C. for 15 hours. After adding 25 ml water and 100 ml dichloromethane, separate the organic phase and extract the aqueous phase three times with 100 ml dichloromethane each time. Dry the combined organic extracts over sodium sulphate, filter and concentrate by vacuum evaporation. Chromatograph the residue on silica gel (solvent: cyclohexane/dichloromethane 1:1). 9.6 g (59% of theor.) of the target compound is obtained.

後処理

  1. customAs in a procedure described in the literature [D. Dauzonne, Synthesis, 1990, 66-70]
  2. customseparate the organic phase
  3. extractionextract the aqueous phase three times with 100 ml dichloromethane each time
  4. dry with materialDry the combined organic extracts over sodium sulphate
  5. filtrationfilter
  6. concentrationconcentrate by vacuum evaporation
  7. custom9.6 g (59% of theor.) of the target compound is obtained

出典と根拠

ORDレコード
ord-56987c0d79654ba9af5c7415de26a595
出典データセット
uspto-grants-2012_05
特許番号
US08183246B2

反応ノート

読み込み中…