Dimethyl Sulfoxide → 3-(2-Bromo-6-nitrophenyl)-2-propenenitrile

HRID 1005668노트

반응식

HRID 1005668 반응식
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[CH:4]=O.[O-2].[Mg+2].CS(C)=O.[C:19]([CH2:21]P(=O)(OCC)OCC)#[N:20]>C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[CH:4]=[CH:21][C:19]#[N:20]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 6850729Magnesium monoxideHCID 150631742-Bromo-6-nitrobenzaldehyde

생성물 1

HCID 684976623-(2-Bromo-6-nitrophenyl)-2-propenenitrile

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

After stirring 2-bromo-6-nitrobenzaldehyde (30.4 g), magnesium oxide (75 g) and dimethyl sulfoxide (11.3 ml) sufficiently for 1 minute, diethyl (cyanomethyl)phosphonate (25.8 ml) was added thereto and the mixture was stirred for further 2 hours. After the completion of stirring, the mixture was left stand overnight. Then, ethyl acetate was added thereto, and the mixture was stirred and then filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography (ethyl acetate), to give 32 g of 3-(2-bromo-6-nitrophenyl)-2-propenenitrile (E-isomer:Z-isomer=3:1).

후처리

  1. stirringAfter the completion of stirring
  2. waitthe mixture was left stand overnight
  3. stirringthe mixture was stirred
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-ec68f06b9c7c4b0394e797bffca3aad2
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06787534B2

반응 노트

불러오는 중…