Sodium Cyanide → 2,4-Dibromo-6-cyanomethylanisole

HRID 444101Notes

Reaction equation

HRID 444101 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([CH2:9]Br)[C:3]=1[O:11][CH3:12].[C-:13]#[N:14].[Na+]>C(O)C.O>[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([CH2:9][C:13]#[N:14])[C:3]=1[O:11][CH3:12]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 205361872,4-Dibromo-6-bromomethylanisole

Product 1

HCID 205361852,4-Dibromo-6-cyanomethylanisole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of the product of stage (c) (183 g) in ethanol (150 ml) was heated to reflux. A solution of sodium cyanide (25 g) in hot water (50 ml) was added which maintained gentle refluxing. The mixture was then stirred for 5 minutes, poured into ice water, and the product was filtered off, taken up in dichloromethane, washed with water, dried over magnesium sulphate and filtered. The solvent was removed to give a brown oil which slowly crystallised. Recrystallisation from petroleum ether gave the title product as colourless needles, mp 87°-88° C.

Workup

  1. temperaturemaintained gentle refluxing
  2. filtrationthe product was filtered off
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customThe solvent was removed
  7. customto give a brown oil which
  8. customslowly crystallised
  9. customRecrystallisation from petroleum ether

Sources & evidence

ORD record
ord-7f5418c144304f2484d21252fe552bae
Source dataset
uspto-grants-1981_04
Patent number
US04263037

Reaction notes

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