(Pentafluorophenyl)hydrazine → 2-(2,3,4,5-Tetramethylcyclopentadienyl)benzaldehyde pentafluorophenylhydrazone

HRID 15711Notes

Reaction equation

HRID 15711 reaction equation
[CH3:1][C:2]1[CH:3]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=O)[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7].[F:18][C:19]1[C:24]([NH:25][NH2:26])=[C:23]([F:27])[C:22]([F:28])=[C:21]([F:29])[C:20]=1[F:30]>C(O)C>[F:18][C:19]1[C:24]([NH:25][N:26]=[CH:12][C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[CH:3]2[C:2]([CH3:1])=[C:6]([CH3:7])[C:5]([CH3:8])=[C:4]2[CH3:9])=[C:23]([F:27])[C:22]([F:28])=[C:21]([F:29])[C:20]=1[F:30]

Participants

4

Reactant 2

HCID 13236(Pentafluorophenyl)hydrazineHCID 1317271152-(2,3,4,5-Tetramethylcyclopentadienyl)benzaldehyde

Product 1

HCID 1317271252-(2,3,4,5-Tetramethylcyclopentadienyl)benzaldehyde pentafluorophenylhydrazoneYield 98.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(2,3,4,5-tetramethylcyclopentadienyl)benzaldehyde (10.0 mmol) in ethanol (60.0 mL) was added dropwise pentafluorophenylhydrazine (11.0 mmol) under a nitrogen atmosphere. The mixture was stirred at room temperature for 2 hrs. The solvent was distilled off under reduced pressure and the residue was recrystallized from hexane to give 2-(2,3,4,5-tetramethylcyclopentadienyl)benzaldehyde pentafluorophenylhydrazone (4.00 g, yield 97.0%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-dc375aa7eddc41199c660968bb8f20f0
Source dataset
uspto-grants-2010_06
Patent number
US07732643B2

Reaction notes

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