Sodium Cyanide → 2-(2,2,2-Trifluoroethoxy)-3-chlorophenylacetonitrile

HRID 1740604Notes

Reaction equation

HRID 1740604 reaction equation
[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7]Br.[C-:16]#[N:17].[Na+]>CN(C=O)C>[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][C:16]#[N:17]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 187001832-(2,2,2-Trifluoroethoxy)-3-chlorobenzyl bromide

Product 1

HCID 540256162-(2,2,2-Trifluoroethoxy)-3-chlorophenylacetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2,2,2-trifluoroethoxy)-3-chlorobenzyl bromide (1.6 g, 5.4 mmol) from Step 2 above in DMF (12 mL) was added NaCN (0.28 g, 5.7 mmol). The solution was stirred at ambient temperature for 14 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using a gradient elution of 5-20% EtOAc:hexanes to give 2-(2,2,2-trifluoroethoxy)-3-chlorophenylacetonitrile as a colorless oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by pressurized silica gel column chromatography
  7. washa gradient elution of 5-20% EtOAc

Sources & evidence

ORD record
ord-eb1983998d494097aa1b915ac9d20222
Source dataset
uspto-grants-1999_10
Patent number
US05968938

Reaction notes

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