Trimethylsilyl cyanide → 3-Chloro-4-fluorobenzyl cyanide

HRID 2277593Notes

Reaction equation

HRID 2277593 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([Cl:10])[CH:4]=1.C[Si]([C:15]#[N:16])(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CC#N>[Cl:10][C:5]1[CH:4]=[C:3]([CH2:2][C:15]#[N:16])[CH:8]=[CH:7][C:6]=1[F:9]

Participants

5

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 27575424-(Bromomethyl)-2-chloro-1-fluorobenzene

Product 1

HCID 27737253-Chloro-4-fluorobenzyl cyanideYield 60.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-bromomethyl-2-chloro-1-fluoro-benzene (3.7 g, 16.5 mmol) in CH3CN (30 mL) was added trimethylsilyl cyanide (2.1 mL) and TBAF (4.8 g, 18.4 mmol). The resulting mixture was heated at reflux for 30 min. After cooling of the mixture to room temperature, it was extracted with EtOAc. The organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was then purified by silica gel flash column chromatography to give the title compound (1.7 g, 60.7%) as an oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 30 min
  3. extractionit was extracted with EtOAc
  4. washThe organic layer was washed with brine
  5. customdried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo
  8. customto give a crude product which
  9. customwas then purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-c640d9ef4c2c450fbb24368abb051bb0
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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