Sodium Cyanide → 2,3,6-Trifluorophenylacetonitrile

HRID 1638680Notes

Reaction equation

HRID 1638680 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 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-c8cdabf856714ec99083d7b88f92ab5c
Source dataset
uspto-grants-1989_11
Patent number
US04880806

Reaction notes

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