Potassium Cyanide → 2-(3-Bromo-5-fluorophenyl)acetonitrile

HRID 50742Notes

Reaction equation

HRID 50742 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5]Br.[C-:11]#[N:12].[K+]>O1CCOCC1.O.CCO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][C:11]#[N:12])[CH:7]=[C:8]([F:10])[CH:9]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 235096191-Bromo-3-(bromomethyl)-5-fluorobenzene

Product 1

HCID 235096352-(3-Bromo-5-fluorophenyl)acetonitrile

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-bromo-5-fluorobenzyl bromide (3.2 g, 0.0112 mole) in 1,4-dioxane (20 mL) was added a solution of KCN (0.82 g, 0.013 mole) in H2O (5 mL) and EtOH (5 mL), refluxed for 2 hours, extracted with ether, washed with brine, dried over MgSO4, and concentrated. Column chromatography was performed using hexane/ethyl acetate (19:1). 3-Bromo-5-fluorophenylacetonitrile was obtained was a colorless oil: 1H NMR (DMSO-d6) δ 4.15 (s, 2H), 7.29 (d, 1H, J=9.37 Hz), 7.47 (s, 1H), 7.55 (d, 1H, J=8.45 Hz); MS(EI) M+m/z 213; Anal. Calc. For C8H5BrFN: C, 44.89; H, 2.35; N, 6.54. Found: C, 44.88; H, 2.32; N, 6.46.

Workup

  1. temperaturerefluxed for 2 hours
  2. extractionextracted with ether
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f3f8272508164efd9a63a05732de4504
Source dataset
uspto-grants-2004_03
Patent number
US06713478B2

Reaction notes

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