Potassium Cyanide → 2-(4-Bromo-2,6-difluorophenyl)acetonitrile

HRID 576195Notes

Reaction equation

HRID 576195 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([CH2:9]Br)=[C:6]([F:8])[CH:7]=1.[C-:12]#[N:13].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([CH2:9][C:12]#[N:13])=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 27733055-Bromo-2-(bromomethyl)-1,3-difluorobenzene

Product 1

HCID 27733112-(4-Bromo-2,6-difluorophenyl)acetonitrileYield 45.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-bromo-2-(bromomethyl)-1,3-difluorobenzene (1.6 g, 5.60 mmol) in DMF (20 mL) was added KCN (0.401 g, 6.16 mmol). The resulting mixture was stirred at 25° C. for 16 h. The mixture was dissolved in H2O (50 mL) and extracted by EA (50 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by silica column chromatography (PE/EA=3/1) to yield a white solid of 2-(4-bromo-2,6-difluorophenyl)acetonitrile (1.1 g, 2.57 mmol, 45.9% yield): 1H NMR (400 MHz, CD3OD) δ 7.39-7.36 (m, 2H), 3.89 (s, 2H).

Workup

  1. extractionextracted by EA (50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by silica column chromatography (PE/EA=3/1)

Sources & evidence

ORD record
ord-e5d80b4e94244175bee74194dca75c47
Source dataset
uspto-grants-2015_05
Patent number
US09035063B2

Reaction notes

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