Sodium Cyanide → 2,3,6-Trifluorophenylacetonitrile

HRID 2351909Notes

Reaction equation

HRID 2351909 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-8f809ca2d3684efd8a04c459bd7e0292
Source dataset
uspto-grants-1989_10
Patent number
US04874764

Reaction notes

Loading…