Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → 3-(4-Bromo-2,6-difluoro-phenyl)-acrylic acid ethyl ester

HRID 1011658Notes

Reaction equation

HRID 1011658 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([F:10])[C:5]([CH:6]=O)=[C:4]([F:11])[CH:3]=1.[C:12]([CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:14][CH2:15][CH3:16])=[O:13]>C1(C)C=CC=CC=1>[CH2:15]([O:14][C:12](=[O:13])[CH:17]=[CH:6][C:5]1[C:8]([F:10])=[CH:9][C:2]([Br:1])=[CH:3][C:4]=1[F:11])[CH3:16]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 27732904-Bromo-2,6-difluorobenzaldehyde

Product 1

HCID 673146253-(4-Bromo-2,6-difluoro-phenyl)-acrylic acid ethyl esterYield 91.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-bromo-2,6-difluoro-benzaldehyde (1 g, 4.5 mmol), (carbethoxymethylene)-triphenyl-phosphorane (2 g, 5.7 mmol) in 30 mL of toluene was heated at reflux for 6 hours, and was evaporated to dryness. The solid was stirred in 200 mL of petroleum ether, and was filtered. The filtrate was evaporated to give the product as oil (1.2 g, yield 91%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. customwas evaporated to dryness
  4. filtrationwas filtered
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-f304211debce41509615a380ce5d43fe
Source dataset
uspto-grants-2011_07
Patent number
US07977372B2

Reaction notes

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