Hydrochloric Acid → 2-((3-Fluoro-5-methoxyphenyl)(methoxy)methylene)malononitrile

HRID 731842Notes

Reaction equation

HRID 731842 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[H-].[Na+].[F:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1)[C:12](Cl)=[O:13].Cl.[CH2:21]1COCC1>>[F:8][C:9]1[CH:10]=[C:11]([C:12]([O:13][CH3:21])=[C:2]([C:1]#[N:5])[C:3]#[N:4])[CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 866170143-Fluoro-5-methoxybenzoyl chloride

Product 1

HCID 866170152-((3-Fluoro-5-methoxyphenyl)(methoxy)methylene)malononitrile

Procedure

A solution of malononitrile (2.87 g, 0.044 mmol) in dry THF (50 ml) was stirred at 0° C. under an argon atmosphere. NaH in paraffin oil (4.64 g, 0.116 mol) was added piece-wise to solution. 3-fluoro-5-methoxybenzoyl chloride (BA67, 0.029 mol) was dissolved in 50 ml dry THF and added slowly to reaction. Reaction was warmed to room temperature and stirred under argon for 24 hours. 1N HCl (200 ml) was slowly added, then reaction mixture was extracted with EtOAc. Organic phases were combined, dried with magnesium sulfate, then concentrated in vacuo to yield 2-((3-fluoro-5-methoxyphenyl)(methoxy)methylene)malononitrile (BA69).

Workup

  1. additionadded slowly to reaction
  2. customReaction
  3. customreaction mixture
  4. extractionwas extracted with EtOAc
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-437f6b83268f41ac96300a835cd70b5e
Source dataset
uspto-grants-2009_09
Patent number
US07585868B2

Reaction notes

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