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

HRID 1155976Notes

Reaction equation

HRID 1155976 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-696e7177b0634e3584ddd9965c0848bf
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

Loading…