Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 67539176, compound

HRID 2240933Notes

Reaction equation

HRID 2240933 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=O.[CH3:11][O:12][C:13](=[O:34])[CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[CH3:11][O:12][C:13](=[O:34])[CH:14]=[CH:7][C:6]1[CH:9]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:10]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 67539176HCID 67539176, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
95 °C

Procedure

A solution of 5-Bromo-2-fluoro-benzaldehyde (1.0 g, 4.9 mmol) in anhydrous acetonitrile (20.0 mL) was added methyl(triphenylphosphoranylidene)acetate (3.3 g, 9.0 mmol) and heated to 95° C. for 12 h. The mixture was cooled, filtered and concentrated under reduced pressure. Silica gel chromatography (5% Ethyl acetate/petroleum ether) gave the title compound as a white solid (1.27 g, 99%) which was used directly in the next step.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2452180692a54fe8a2df2d52b3e6055d
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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