(Triphenylphosphoranylidene)acetaldehyde → 3-(3-Bromo-4,5-dimethoxyphenyl)-propenal

HRID 1453997Notes

Reaction equation

HRID 1453997 reaction equation
[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=O.C1(P(=[CH:33][CH:34]=[O:35])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=[CH:33][CH:34]=[O:35])[CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[O:12][CH3:13]

Participants

4

Reactant 2

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 813793-Bromo-4,5-dimethoxybenzaldehyde

Product 1

HCID 858878623-(3-Bromo-4,5-dimethoxyphenyl)-propenalYield 45%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5-bromoveratraldehyde (100 mg, 0.41 mmol) and (triphenylphosphoranylidene)acetaldehyde (137 mg, 0.45 mmol) in dry benzene (2.5 ml) was refluxed for 9 h and the solvent was removed. The crude product was passed through a short silica gel column (bond-elute) (eluents: 10% ethyl acetate in hexane), giving 3-(3-bromo-4,5-dimethoxy-phenyl)-propenal (50 mg, 45%). 1H NMR (CDCl3): 9.68 (d, J=7.6 Hz, 1H), 7.36 (d, J =1.8 Hz, 1H), 7.34 (d, J=15.8 Hz, 1H), 7.03 (d, J=1.9 Hz, 1H), 6.62 (dd, J=7.6, 16.0 Hz, 1H), 3.913 (s, 3H), 3.907 (s, 3H) (the sample contained trace amount of starting material).

Workup

  1. temperaturewas refluxed for 9 h
  2. customthe solvent was removed
  3. washThe crude product was passed through a short silica gel column (bond-elute) (eluents: 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-0b50bad2b4b94b40981fa994dc158bc8
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

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