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

HRID 1005668Notes

Reaction equation

HRID 1005668 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-ec68f06b9c7c4b0394e797bffca3aad2
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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