Malononitrile → 2,2-Bis-(2,2,2-trifluoro-ethyl)-malononitrile

HRID 12509

Reaction equation

HRID 12509 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].IC[CH2:8][C:9]([F:12])([F:11])[F:10].[H-].[Na+]>C1COCC1>[F:10][C:9]([F:12])([F:11])[CH2:8][C:2]([CH2:8][C:9]([F:12])([F:11])[F:10])([C:1]#[N:5])[C:3]#[N:4]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 24758Sodium hydrideHCID 1561651,1,1-Trifluoro-3-iodopropane

Product 1

HCID 866254102,2-Bis-(2,2,2-trifluoro-ethyl)-malononitrileYield 16.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Malononitril (20.15 mmol) and 1-iodo-3,3,3-trifluoropropane (42.65 mmol) were dissolved in 30 ml dry THF, and the mixture was cooled with an ice/salt bath. 1.61 g NaH (40.3 mmol) was added portionwise, keeping the temperature below 5° C. The reaction mixture was stirred at room temperature for 2 hours and evaporated under reduced pressure. The crude material was purified by flash chromatography eluting with DCM, yielding 0.76 grams of an oil. 1H NMR (400 MHz, CDCl3) δ 2.62-2.49 (m, 4H), 2.31-2.24 (m, 4H)

Workup

  1. temperaturethe mixture was cooled with an ice/salt bath
  2. customthe temperature below 5° C
  3. customevaporated under reduced pressure
  4. customThe crude material was purified by flash chromatography
  5. washeluting with DCM

Sources & evidence

ORD record
ord-a23d62bb03b44b8aa4bbb58712329041
Source dataset
uspto-grants-2010_06
Patent number
US07728018B2

Linked notes

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