Potassium Cyanide → 2,6-Difluoro-4-methoxyphenylacetonitrile

HRID 514227Notes

Reaction equation

HRID 514227 reaction equation
[C-:1]#[N:2].[K+].[F:4][C:5]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]([F:15])[C:6]=1[CH2:7]Br.C([O-])(O)=O.[Na+]>O.CN(C)C=O>[F:4][C:5]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]([F:15])[C:6]=1[CH2:7][C:1]#[N:2]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 33542722,6-Difluoro-4-methoxybenzyl bromide

Product 1

HCID 38695002,6-Difluoro-4-methoxyphenylacetonitrileYield 98.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6228DimethylformamideSolvent

Procedure

A solution of KCN (0.88 g, 13 mmol) dissolved in water (2 mL) was added dropwise to a water-bath-cooled solution of 2,6-difluoro-4-methoxybenzyl bromide (2.50 g, 10.5 mmol) in N,N-dimethylformamide (10 mL). The reaction mixture was stirred for 20 min. Water was added (20 mL) and then the reaction mixture was poured into saturated aqueous NaHCO3 solution (20 mL) and extracted with ether (50 mL). The organic phase was washed with water (5×25 mL), dried over MgSO4, and concentrated to give an oil, which crystallized on standing to provide the title compound as a white solid (1.9 g).

Workup

  1. extractionextracted with ether (50 mL)
  2. washThe organic phase was washed with water (5×25 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give an oil, which
  6. customcrystallized

Sources & evidence

ORD record
ord-d0076ca15be84ba8a11d935432022e48
Source dataset
uspto-grants-2015_08
Patent number
US09107412B2

Reaction notes

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