Malononitrile → 2-[(3-Bromophenyl)methylene]propanedinitrile

HRID 1635040Notes

Reaction equation

HRID 1635040 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10](#[N:14])[CH2:11][C:12]#[N:13].N1CCCCC1>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:11]([C:10]#[N:14])[C:12]#[N:13])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8082PiperidineHCID 765833-Bromobenzaldehyde

Product 1

HCID 3675262-[(3-Bromophenyl)methylene]propanedinitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In this situation the aldehyde, such as 3-bromobenzaldehyde as a representative example, is reacted with malononitrile in the presence of catalytic piperidine in a solvent such as dioxane to afford the 2-[(3-bromophenyl)methylene]malononitrile. Epoxide formation proceeds readily with commercial bleach at a pH of 5 to 6. Treatment with hydrobromic acid in methanol then affords the required methyl 2-bromo-2-(3-bromophenyl)acetate. Similarly prepared was methyl 2-bromo-2-(3-cyanophenyl)acetate

Sources & evidence

ORD record
ord-c2c95f95d13f4051abfa6fb92f4071b8
Source dataset
uspto-grants-2003_01
Patent number
US06509335B1

Reaction notes

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