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

HRID 1173113노트

반응식

HRID 1173113 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(OC(=O)C)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

2-Bromo-6-nitrobenzaldehyde (30.4 g), magnesium oxide (75 g) and dimethyl sulfoxide (11.3 ml) were sufficiently stirred for one minute. Then, to the mixture was added diethyl (cyanomethyl)phosphonate (25.8 ml) and the mixture was stirred for further 2 hours. The stirring was stopped and the reaction mixture was allowed to stand overnight. Thereafter, ethylacetate was added thereto and the resulting mixture was stirred, followed by filtering. 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. waitto stand overnight
  2. stirringthe resulting mixture was stirred
  3. filtrationby filtering
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-846cdc69738f4ee084959a17b37225ce
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834049B2

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