Sodium Cyanide → 2-(Trifluoromethoxy)phenylacetonitrile

HRID 2289317Notes

Reaction equation

HRID 2289317 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]Br.[C-:14]#[N:15].[Na+]>CN(C=O)C>[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][C:14]#[N:15]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 27772542-(Trifluoromethoxy)benzyl bromide

Product 1

HCID 27773212-(Trifluoromethoxy)phenylacetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-trifluoromethoxybenzyl bromide (0.95 g, 3.9 mmol) from Step 2 above in DMF (5 mL) was added NaCN (0.21 g, 4.3 mmol). The mixture was stirred at ambient temperature for 14 h and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 15% EtOAc-hexanes as eluant to give 2-trifluoromethoxyphenylacetonitrile as a colorless liquid (TLC Rf =0.6 (solvent)).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was purified by pressurized silica gel column chromatography

Sources & evidence

ORD record
ord-8f1d8a84fd2d4d6ebb75db4419a0f787
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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