Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 3-(4-bromo-3-fluorophenyl)prop-2-enoate

HRID 1011657Notes

Reaction equation

HRID 1011657 reaction equation
[C:1]([CH:6]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3][CH2:4][CH3:5])=[O:2].[Br:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][C:28]=1[F:35]>C(Cl)Cl>[CH2:4]([O:3][C:1](=[O:2])[CH:6]=[CH:31][C:30]1[CH:33]=[CH:34][C:27]([Br:26])=[C:28]([F:35])[CH:29]=1)[CH3:5]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 27834114-Bromo-3-fluorobenzaldehyde

Product 1

HCID 67313932Ethyl 3-(4-bromo-3-fluorophenyl)prop-2-enoateYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (carbethoxymethylene)-triphenylphosphorane (4.2 g, 12 mmol) in CH2Cl2 at 10 degrees Celsius was added 4-bromo-3-fluoro-benzaldehyde (2.3 g, 11.4 mmol) dropwise over 30 minutes. This mixture was stirred for another 45 minutes at room temperature until the starting material had been consumed, and then the solvent was removed in vacuo. The crude product was purified by column chromatography (PET:EtOAc=1:1) to get desired product (2.69 g, 87%).

Workup

  1. customhad been consumed
  2. customthe solvent was removed in vacuo
  3. customThe crude product was purified by column chromatography (PET:EtOAc=1:1)

Sources & evidence

ORD record
ord-f628c77220ae44e78ab8e36a40d741c2
Source dataset
uspto-grants-2011_07
Patent number
US07977372B2

Reaction notes

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