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

HRID 1926899노트

반응식

HRID 1926899 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매2회HCID 6344Dichloromethane용매HCID 7237O-Xylene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-56987c0d79654ba9af5c7415de26a595
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183246B2

반응 노트

불러오는 중…