Malononitrile → [(5-Chloro-2-Thenoyl)Methyl]Malononitrile

HRID 374524

Reaction equation

HRID 374524 reaction equation
Br[CH2:2][C:3]([C:5]1[S:6][C:7]([Cl:10])=[CH:8][CH:9]=1)=[O:4].[C:11](#[N:15])[CH2:12][C:13]#[N:14].CC(C)([O-])C.[K+]>O1CCCC1>[Cl:10][C:7]1[S:6][C:5]([C:3]([CH2:2][CH:12]([C:11]#[N:15])[C:13]#[N:14])=[O:4])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 20636342-(Bromoacetyl)-5-chlorothiopheneHCID 23665647Potassium tert-butoxide

Product 1

HCID 15296965[(5-Chloro-2-Thenoyl)Methyl]Malononitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-bromo-1-(5-chloro-2-thienyl)ethanone (11.50 g, 48 mmol) in tetrahydrofuran is added to a solution of malononitrile (3.17 g, 48 mmol) and potassium tert-butoxide (5.70 g, 51 mmol) in tetrahydrofuran at 0° C. The reaction mixture is stirred for several minutes, concentrated in vacuo, diluted with water and filtered to collect solids. Flash chromatography of the solids using silica gel and a (4:1) hexane/ethyl acetate solution gives the title compound as a yellow solid, mp 155°-158° C.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with water
  3. filtrationfiltered
  4. customto collect solids

Sources & evidence

ORD record
ord-78cc26c5a86c4e45a082a76a41161c4b
Source dataset
uspto-grants-1996_01
Patent number
US05480902

Linked notes

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