Sodium Cyanide → HCID 68614664, compound

HRID 2189139Notes

Reaction equation

HRID 2189139 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([Cl:9])=[CH:4][C:3]=1[CH2:10]Br.[C-:12]#[N:13].[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([Cl:9])=[CH:4][C:3]=1[CH2:10][C:12]#[N:13]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 68614659HCID 68614659, compound

Product 1

HCID 68614664HCID 68614664, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1 mmol of 1-bromo-2-bromomethyl-4-chloro-5-fluoro-benzene and 4 mmol of sodium cyanide in 3 ml of dry N,N-dimethylformamide is stirred at room temperature till complete conversion is observed. The reaction mixture is quenched by the addition of water and the mixture is extracted with tert-butyl-methyl ether. The combined organic phases are washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (SiO2 60 F) to afford the title compound which is identified based on the Rf value.

Workup

  1. customThe reaction mixture is quenched by the addition of water
  2. extractionthe mixture is extracted with tert-butyl-methyl ether
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-9762304915b64c659ba1f5bdf282caf3
Source dataset
uspto-grants-2012_12
Patent number
US08324235B2

Reaction notes

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