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

HRID 1278694Notes

Reaction equation

HRID 1278694 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH2:7]Br.[C-:11]#[N:12].[K+]>O1CCOCC1.O.C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH2:7][C:11]#[N:12])[CH:9]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 135532954-Bromo-2-(bromomethyl)-1-fluorobenzene

Product 1

HCID 235096312-(5-Bromo-2-fluorophenyl)acetonitrile

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

5-Bromo-2-fluorobenzyl bromide (8.0 g, 0.03 mole) was dissolved in 1,4-Dioxane (60 mL) and added to a solution of KCN (2.04 g, 0.031 mole) in H2O (20 mL) and ethanol ( 20 mL). The resulting mixture was heated under reflux for 5 h. After cooling to rt, the product was extracted with ether ( 200 mL), washed with brine, dried over MgSO4, concentrated. Crystallized from ether/hexane to give 5-bromo-2-fluorophenylacetonitrile as a white crystalline material (5.6 g, 88%): rp 55-58° C.; 1H NMR (DMSO-d6) □ 4.07 (s, 2H), 7.29( t, 1H,J=9.23 Hz), 7.60-7.69( m, 2H); MS(EI) M+ m/z 213 ; Anal. Calc. For C8H5Br2FN: C, 44.89, H, 2.35, N, 6.54. Found: C, 44.90, H, 2.24, N, 6.43.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 5 h
  3. extractionthe product was extracted with ether ( 200 mL)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customCrystallized from ether/hexane

Sources & evidence

ORD record
ord-5c35319bd86440b38b5c85c6f234a165
Source dataset
uspto-grants-2002_09
Patent number
US06444668B1

Reaction notes

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