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Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 3-(6-Bromopyridin-3-yl)acrylic acid methyl ester

HRID 2265933
Notes
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Reaction equation

HRID 2265933 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=O)=[CH:4][CH:3]=1.[CH3:10][O:11][C:12](=[O:33])[CH:13]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:10][O:11][C:12](=[O:33])[CH:13]=[CH:8][C:5]1[CH:6]=[N:7][C:2]([Br:1])=[CH:3][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 714275823-(6-Bromopyridin-3-yl)acrylic acid methyl esterYield 97.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 6-bromo-pyridine-3-carboxaldehyde (300 mg, 1.61 mmol) in toluene was added methyl(triphenylphosphoranylidene)acetate (647 mg, 1.94 mmol) and the solution was refluxed for 6 hrs. The reaction mixture was diluted with EtOAc and then washed three times with H2O, brine, dried. Na2SO4, filtered and concentrated under reduced pressure. The obtained residue was column-chromatographed to yield 3-(6-bromo-pyridin-3-yl)-acrylic acid methyl ester (380 mg, 97%).

Workup

  1. temperaturethe solution was refluxed for 6 hrs
  2. washwashed three times with H2O, brine
  3. customdried
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was column-chromatographed

Sources & evidence

ORD record
ord-92cf8f676a2349658c1d0134543aa6ac
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07858621B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes