Sodium Cyanide → 2,3,6-Trifluorophenylacetonitrile

HRID 2107601Notes

Reaction equation

HRID 2107601 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-06fc2dde16c241dbb20200937d01fed6
Source dataset
uspto-grants-1990_06
Patent number
US04935420

Reaction notes

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