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

HRID 1453069Notes

Reaction equation

HRID 1453069 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].[K+]>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 9032Potassium CyanideHCID 27336604-Bromo-2-fluorobenzyl bromide

Product 1

HCID 71723082-(4-Bromo-2-fluorophenyl)acetonitrileYield 87.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-bromo-1-(bromomethyl)-2-fluorobenzene (5.0 g, 18.7 mmol) in DMF (80 mL) and H2O (8 mL) was added KCN (1.21 g, 18.7 mmol). The mixture was heated to 40° C. for 3 hours before it was cooled down to room temperature. The reaction was diluted with H2O (40 mL) and extracted with Et2O (3×100 mL). The combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed and the residue was purified by flash column chromatography (0-15% EtOAc in hexanes) to give the product (3.5 g, 87% yield). 1H NMR (300 MHz, CDCl3) δ: 3.72 (s, 2H), 7.26-7.35 (m, 3H).

Workup

  1. temperaturewas cooled down to room temperature
  2. extractionextracted with Et2O (3×100 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed
  6. customthe residue was purified by flash column chromatography (0-15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ee48cd856c744c1aa34ec7427d49f1f1
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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