Hydrogen Bromide → HCID 19790388, compound

HRID 2372920Notes

Reaction equation

HRID 2372920 reaction equation
[BrH:1].[Cl:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[Cl:17])[C:6](=O)[CH2:7][CH:8]([C:11]#[N:12])[C:9]#[N:10]>CCOCC.C(Cl)(Cl)Cl>[Br:1][C:9]1[NH:10][C:6]([C:5]2[CH:14]=[CH:15][C:16]([Cl:17])=[C:3]([Cl:2])[CH:4]=2)=[CH:7][C:8]=1[C:11]#[N:12]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 10857979Propanedinitrile, [2-(3,4-dichlorophenyl)-2-oxoethyl]-

Product 1

HCID 19790388HCID 19790388, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

Hydrogen bromide gas is bubbled through a mixture of (3,4-dichlorophenacyl)malononitrile (10.0 g, 0.0395 mol) in ether (150 mL) and chloroform (100 mL) at a moderate rate, keeping the reaction mixture temperature below 35°-40° C. After ten minutes, TLC shows the reaction is complete by UV analysis. The reaction mixture is poured into an ice-water mixture, the layers are separated and the aqueous layer is extracted with ether. The combined organic layer and ether extracts are dried and concentrated in vacuo to give a brown solid. The brown solid is washed with methylene chloride and filtered to obtain the title compound as an off-white solid (3.0 g, 24%, mp >200° C.) which is identified by IR and NMR spectral analyses.

Workup

  1. customthe reaction mixture temperature below 35°-40° C
  2. waitAfter ten minutes
  3. customthe layers are separated
  4. extractionthe aqueous layer is extracted with ether
  5. dry with materialThe combined organic layer and ether extracts are dried
  6. concentrationconcentrated in vacuo
  7. customto give a brown solid
  8. washThe brown solid is washed with methylene chloride
  9. filtrationfiltered

Sources & evidence

ORD record
ord-db37f8417f2541b684e9f6c6171fc4e5
Source dataset
uspto-grants-1992_03
Patent number
US05101042

Reaction notes

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