3-Nitrobenzaldehyde → Methyl 4-[2-(3-nitrophenyl)vinyl]benzoate

HRID 1160384

Reaction equation

HRID 1160384 reaction equation
[Br-].[CH3:2][O:3][C:4]([C:6]1[CH:31]=[CH:30][C:9]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][CH:7]=1)=[O:5].[N+:32]([C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=1)[CH:38]=O)([O-:34])=[O:33].C1CC23[N+](=[N-])C(CCC2)=C3C1>C(#N)C>[N+:32]([C:35]1[CH:36]=[C:37]([CH:38]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]([C:4]([O:3][CH3:2])=[O:5])=[CH:31][CH:30]=2)[CH:40]=[CH:41][CH:42]=1)([O-:34])=[O:33]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromideHCID 219219891,5-Diazobicyclo(4.3.0)non-5-ene

Product 1

HCID 68690726Methyl 4-[2-(3-nitrophenyl)vinyl]benzoateYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

71.2 g of 4-methoxycarbonylbenzyltriphenylphosphonium bromide and 23 g (0.15 M) of 3-nitrobenzaldehyde are added to 360 ml of acetonitrile in a 1000 ml reactor. 19 ml (0.15 M) of 1,5-diazobicyclo[4.3.0]non-5-ene (DBN) are then added and the reaction medium is then refluxed with stirring for 1 hour. The solvent is then evaporated off and the residue obtained is then purified by chromatography on silica, using dichloromethane as eluent. After evaporation, 41.6 g of a white solid are obtained (yield: 95%).

Workup

  1. temperaturethe reaction medium is then refluxed
  2. customThe solvent is then evaporated off
  3. customthe residue obtained
  4. customis then purified by chromatography on silica
  5. customAfter evaporation, 41.6 g of a white solid
  6. customare obtained (yield: 95%)

Sources & evidence

ORD record
ord-db25ae22fe1a45c58be3ca0a56c10117
Source dataset
uspto-grants-2010_10
Patent number
US07816397B2

Linked notes

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