Malononitrile → (2-Fluorobenzylidene)malononitrile

HRID 31165

Reaction equation

HRID 31165 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[F:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=O.N1CCCCC1>C(OC(C)C)(=O)C>[F:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=[C:2]([C:1]#[N:5])[C:3]#[N:4]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8082PiperidineHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 17606(2-Fluorobenzylidene)malononitrileYield 28.3%

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Procedure

Malononitrile (3.303 g, 50 mmol), 2-fluorobenzaldehyde (6.205 g, 50 mmol), 1 g of molecular sieves, and 500 mg of a resin bound piperidine (described in Tetrahedron Lett., 1999, 40, 7031-33) were placed in a vessel which was irradiated in a 300 W single mode microwave for 15 seconds. The reaction mixture was taken up in iso-propyl acetate, filtered, evaporated, taken up in dichloromethane, filtered through a pad of Magnasol, evaporated, and recrystallized from ethanol to yield 2.435 g of the title material as a crystalline solid,

Workup

  1. customwere placed in a vessel
  2. customwhich was irradiated in a 300 W single mode microwave for 15 seconds
  3. filtrationfiltered
  4. customevaporated
  5. filtrationfiltered through a pad of Magnasol
  6. customevaporated
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8e87faf475de4826847a48546c5fff7a
Source dataset
uspto-grants-2008_09
Patent number
US07425580B2

Linked notes

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