Sodium Cyanide → HCID 54447024, compound

HRID 1740610Notes

Reaction equation

HRID 1740610 reaction equation
[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[CH:12]=[C:11]([F:13])[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[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:6]=1[CH2:7][C:16]#[N:17]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 18700174HCID 18700174, compound

Product 1

HCID 54447024HCID 54447024, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(2,2,2-trifluoroethoxy)-4-fluorobenzyl bromide (0.80 g, 2.7 mmol) from Step 3 above in DMF (14 mL) was added NaCN (0.20 g, 4.0 mmol). The mixture was stirred at ambient temperature for 14 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (100 mL) and saturated aqueous NaHCO3 (2×50 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give 2-(2,2,2-trifluoroethoxy)-4-fluorophenyl-acetonitrile as an oil (HPLC retention time=8.7 min (method A)).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc (100 mL) and saturated aqueous NaHCO3 (2×50 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9ad4ae613a4b4c5995490105b5f1dfe9
Source dataset
uspto-grants-1999_10
Patent number
US05968938

Reaction notes

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