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

HRID 910878Notes

Reaction equation

HRID 910878 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-dc169f5622ad4acab981a6112296c93f
Source dataset
uspto-grants-2011_09
Patent number
US08022250B2

Reaction notes

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