Water → 5-Fluoro-2-(trifluoromethyl)phenylacetonitrile

HRID 1836184Notes

Reaction equation

HRID 1836184 reaction equation
[C-:1]#[N:2].[K+].[F:4][C:5]1[CH:6]=[CH:7][C:8]([C:13]([F:16])([F:15])[F:14])=[C:9]([CH:12]=1)[CH2:10]Br.O>C(O)C.C(OCC)(=O)C>[F:4][C:5]1[CH:6]=[CH:7][C:8]([C:13]([F:16])([F:15])[F:14])=[C:9]([CH2:10][C:1]#[N:2])[CH:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 27375785-Fluoro-2-(trifluoromethyl)benzyl bromide

Product 1

HCID 27376045-Fluoro-2-(trifluoromethyl)phenylacetonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.95 g (30 mmol) of potassium cyanide is added to a solution of 5.14 g (20 mmol) of 5-fluoro-2-trifluoromethylbenzyl bromide in 45 ml of ethanol/8 ml of water, and it is stirred for 64 hours at room temperature. The reaction solution is diluted with ethyl acetate and extracted with saturated sodium bicarbonate solution. The organic phase is washed with water, dried and concentrated by evaporation. The remaining residue is purified by bulb tube distillation and recrystallized. Yield: 3.6 g (89%).

Workup

  1. extractionextracted with saturated sodium bicarbonate solution
  2. washThe organic phase is washed with water
  3. customdried
  4. concentrationconcentrated by evaporation
  5. customThe remaining residue is purified by bulb tube
  6. distillationdistillation
  7. customrecrystallized

Sources & evidence

ORD record
ord-73f62f6db3974626a93749f9b7002eb4
Source dataset
uspto-grants-2004_08
Patent number
US06777409B2

Reaction notes

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