Reaktion #79020

Reaktionsgleichung

3-bromo-5-fluorobenzyl bromide

KCN

→

3-Bromo-5-fluorophenylacetonitrile

Lösungsmittel

1,4-dioxane

H2O

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed for 2 hours
2. 2
   Extraktionextracted with ether
3. 3
   Waschenwashed with brine
4. 4
   Trocknendried over MgSO4
5. 5
   Einengenconcentrated

Vorschrift

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.

Quelle