4-Fluoroaniline → HCID 85910984, compound

HRID 523036Notes

Reaction equation

HRID 523036 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=O>C(O)(C(F)(F)F)=O.C(#N)C>[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[N:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 97314-FluoroanilineHCID 680093-Fluorobenzaldehyde

Product 1

HCID 85910984HCID 85910984, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The reaction of 4-fluoroaniline and 3-fluorobenzaldehyde in TFA and acetonitrile provided the N-3-fluorobenzylidene-4-fluoroaniline. The cyclopentadiene was separately prepared from its dimer dicyclopentadiene. The dimer was heated at 180° C. to give monomer, which was reacted with N-3-fluorobenzylidene-4-fluoroaniline in acetonitrile in presence of TFA to provide the desired difluoro compound 100.

Sources & evidence

ORD record
ord-f059522e65954bd5ba48a5e5e553125a
Source dataset
uspto-grants-2016_05
Patent number
US09334284B2

Reaction notes

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