Potassium Cyanide → HCID 57998826, compound

HRID 1093918Notes

Reaction equation

HRID 1093918 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH2:9]Br)[C:3]=1[Cl:11].[C-:12]#[N:13].[K+]>C(O)C.O>[Br:1][C:2]1[C:3]([Cl:11])=[C:4]([CH2:9][C:12]#[N:13])[C:5]([F:8])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 579988441-Bromo-3-(bromomethyl)-2-chloro-4-fluorobenzene

Product 1

HCID 57998826HCID 57998826, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-bromo-3-bromomethyl-2-chloro-4-fluorobenzene (9.945 g) in absolute ethanol (40 mL) was added dropwise to a solution of potassium cyanide (2.38 g) in water (2 ml) under heating over a period of 30 minutes. The reaction mixture was heated to reflux for 7 hours. The reaction mixture was then allowed to cool and stored at ambient temperature for 16 hours. The mixture was filtered and the filtrate concentrated. The residue was dissolved in ethyl acetate, dried over magnesium sulfate and concentrated to give (3-bromo-2-chloro-6-fluoro-phenyl)-acetonitrile as a pale yellow oil (8.19 g).

Workup

  1. temperatureunder heating over a period of 30 minutes
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 7 hours
  4. temperatureto cool
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate concentrated
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-de79db588f0740caa9a98ff22b6735cf
Source dataset
uspto-grants-2012_03
Patent number
US08133847B2

Reaction notes

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