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

HRID 1173113ノート

反応式

HRID 1173113 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-846cdc69738f4ee084959a17b37225ce
出典データセット
uspto-grants-2010_11
特許番号
US07834049B2

反応ノート

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