Sodium Cyanide → 2,3,6-Trifluorophenylacetonitrile

HRID 1722294Notes

Reaction equation

HRID 1722294 reaction equation
[C-:1]#[N:2].[Na+].[F:4][C:5]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]([F:14])[C:6]=1[CH2:7]Cl>O.[Cl-].C1([N+](CC)(CC)CC)C=CC=CC=1>[F:4][C:5]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]([F:14])[C:6]=1[CH2:7][C:1]#[N:2]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 156318382-(Chloromethyl)-1,3,4-trifluorobenzene

Product 1

HCID 27779562,3,6-TrifluorophenylacetonitrileYield 65.4%

Reagents, catalysts & solvents 2

HCID 5743346N,N,N-Triethylbenzenaminium chlorideCatalystHCID 962WaterSolvent2×

Procedure

To a solution of sodium cyanide (1.94 g) in water (4 ml) is added with phenyltriethylammonium chloride (0.09 g), and thereto is added with stirring 2,3,6-trifluorobenzyl chloride (5.0 g), and the mixture is stirred at 90° to 100° C. for 40 minutes. The reaction mixture is poured into water (20 ml) and is extracted with diethyl ether. The extract is dried over potassium carbonate and the solvent is distilled off to give 2-(2,3,6-trifluorophenyl)acetonitrile (3.1 g), b.p. 80°-85° C. (5 mmHg).

Workup

  1. extractionis extracted with diethyl ether
  2. dry with materialThe extract is dried over potassium carbonate
  3. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-405e6d62e59145ea8ab59923f359a188
Source dataset
uspto-grants-1989_08
Patent number
US04855292

Reaction notes

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