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

HRID 50745Notes

Reaction equation

HRID 50745 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, and crystallized from ether/hexane to give 5-bromo-2-fluorophenylacetonitrile as a white crystalline material (5.6 g, 88%): mp 55-58° C.; 1H NMR (DMSO-d6) δ 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-1649b73e77a84217ac42d82279826440
Source dataset
uspto-grants-2004_03
Patent number
US06713478B2

Reaction notes

Loading…