Sodium Cyanide → 2-(4-Bromo-2-fluorophenyl)acetonitrile

HRID 858692Notes

Reaction equation

HRID 858692 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[C:4]([F:10])[CH:3]=1.[C-:11]#[N:12].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:11]#[N:12])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 27336604-Bromo-2-fluorobenzyl bromide

Product 1

HCID 71723082-(4-Bromo-2-fluorophenyl)acetonitrileYield 46.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-1-bromomethyl-2-fluoro-benzene (100 g, 373 mmol) in DMF (190 mL) and water (10 mL) was added sodium cyanide (22 g, 448 mmol). The reaction was heated to 70 degrees Celsius for 3 hours, concentrated to a volume of 100 mL, and then the solution was diluted with 100 mL of ethyl acetate. After the solids were removed by filtration, water (250 mL) was added and the layers were separated. The organic layer was further washed with 3×100 mL of water. The organic layer was dried over MgSO4, filtered to remove solids, and then concentrated. Purification by distillation gave the desired product (37.124 g, 46%). B.P.=72–75 degrees Celsius.

Workup

  1. temperatureThe reaction was heated to 70 degrees Celsius for 3 hours
  2. concentrationconcentrated to a volume of 100 mL
  3. additionthe solution was diluted with 100 mL of ethyl acetate
  4. customAfter the solids were removed by filtration, water (250 mL)
  5. additionwas added
  6. customthe layers were separated
  7. washThe organic layer was further washed with 3×100 mL of water
  8. dry with materialThe organic layer was dried over MgSO4
  9. filtrationfiltered
  10. customto remove solids
  11. concentrationconcentrated
  12. customPurification
  13. distillationby distillation

Sources & evidence

ORD record
ord-5a2ab9a7572e4409925005ee51c133e1
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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