Water → 2-(4-Bromo-2-fluorophenyl)acetonitrile

HRID 1797209Notes

Reaction equation

HRID 1797209 reaction equation
[C-:1]#[N:2].[Na+].[F:4][C:5]1[CH:12]=[C:11]([Br:13])[CH:10]=[CH:9][C:6]=1[CH2:7]Br.O>CS(C)=O>[Br:13][C:11]1[CH:10]=[CH:9][C:6]([CH2:7][C:1]#[N:2])=[C:5]([F:4])[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 27336604-Bromo-2-fluorobenzyl bromide

Product 1

HCID 71723082-(4-Bromo-2-fluorophenyl)acetonitrileYield 96.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium cyanide (1.37 g, 28.00 mmol) was added to a stirred solution of 2-fluoro-4-bromo benzyl bromide (5.0 g, 18.66 mmol) in dry DMSO (60 mL) at ambient temperature under nitrogen. The reaction was stirred for 4 h at ambient temperature then poured into H2O (150 mL) and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to give the intermediate title compound as a brown oil (3.85 g, 96%). Electrospray mass spectrum: M=213, M+2=215

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3a9352cc77f49d292b5a598f113c945
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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