Sodium Cyanide → 2-(4-Bromo-3-fluorophenyl)acetonitrile

HRID 1879432Notes

Reaction equation

HRID 1879432 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][C:3]=1[F:10].[C-:11]#[N:12].[Na+]>C(O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][C:11]#[N:12])=[CH:4][C:3]=1[F:10]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 116661761-Bromo-4-(bromomethyl)-2-fluorobenzene

Product 1

HCID 116009532-(4-Bromo-3-fluorophenyl)acetonitrileYield 155.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-bromo-3-fluorobenzyl bromide (12.2 g, 0.03 moles) in ethanol (100 ml) is added with NaCN (2 g, 0.04 moles) and refluxed for 2 hours. The mixture is concentrated under vacuum; the resulting residue is taken up with water, then extracted with ethyl acetate. The organic phase is washed with brine, dried over sodium sulfate and concentrated under vacuum to give a dark oil (10 g), which is subjected to chromatography on a silica gel column (150 g), eluting with hexane:ethyl ether 7:3, to afford the product in the solid form.

Workup

  1. temperaturerefluxed for 2 hours
  2. concentrationThe mixture is concentrated under vacuum
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e07ca66264614c369c52d2c4727bddf0
Source dataset
uspto-grants-2012_11
Patent number
US08314268B2

Reaction notes

Loading…