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

HRID 2172649Notes

Reaction equation

HRID 2172649 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 56.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-bromo-3-fluorobenzyl bromide (27 g, 0.1 moles) in ethanol (200 ml) is mixed with NaCN (5.4 g, 0.11 moles) and refluxed for 3 hours. The mixture is concentrated under vacuum; the resulting residue is taken up with water and 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 (12.1 g, 56% yield).

Workup

  1. temperaturerefluxed for 3 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-9fa2d7fbd0bc4714aa9129aadc4495ef
Source dataset
uspto-grants-2015_06
Patent number
US09056818B2

Reaction notes

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