Water → (4-Methoxyphenyl)malononitrile

HRID 481508Notes

Reaction equation

HRID 481508 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:10](#[N:14])[CH2:11][C:12]#[N:13].O>C1COCC1>[C:12]([CH:11]([C:10]#[N:14])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)#[N:13]

Participants

5

Reactant 3

HCID 962WaterHCID 8010MalononitrileHCID 696764-Iodoanisole

Product 1

HCID 641441(4-Methoxyphenyl)malononitrileYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-iodoanisole (2.3 g, 10 mmol), malononitrile (750 mg, 11 mmol) and KOBu-t (2.5 g, 22 mmol) in THF (40 ml) was added PdCl2 (PPh3)2 (300 mg, 0.4 mmol) at room temperature. After the mixture was refluxed for 25 hours, the mixture was poured into H2O (10 ml), and extracted with ether. The combined extracts were dried (Na2SO4), and concentrated to give a yellow oil, which was purified by a column chromatography on silica gel to give Compound 35 as a colorless solid (1.1 g, 64%).

Workup

  1. temperatureAfter the mixture was refluxed for 25 hours
  2. extractionextracted with ether
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customto give a yellow oil, which
  6. customwas purified by a column chromatography on silica gel

Sources & evidence

ORD record
ord-d0b10cb211bf40ed916260b352fa08b7
Source dataset
uspto-grants-1998_08
Patent number
US05789423

Reaction notes

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