Sodium Cyanide → 4-Chlorobenzonitrile

HRID 36782

Reaction equation

HRID 36782 reaction equation
[C-:1]#[N:2].[Na+].F[B-](F)(F)F.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N+]#N)=[CH:12][CH:11]=1>O>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:1]#[N:2])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 110855064-Chlorobenzene-1-diazonium; tetrafluoroboranuide

Product 1

HCID 121634-ChlorobenzonitrileYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Sodium cyanide (2.94 g; 0.06 mol) was added to water and stirred. Cuprous cyanide (2.7 g; 0.03 mol) was added to the mixture stirred until it became homogeneous. 4-chlorobenzenediazonium tetrafluoroborate (5.66 g; 0.025 mol) in water (10 ml) was added to one portion. The mixture was allowed to react at room temperature. The mixture was extracted by ethyl acetate and the extract analysed by means of gas chromatography which indicated that 4-chlorobenzonitrile had been formed in 75% yield.

Workup

  1. stirringstirred until it
  2. customto react at room temperature
  3. extractionThe mixture was extracted by ethyl acetate
  4. customhad been formed in 75% yield

Sources & evidence

ORD record
ord-e6b27fd42fc5429c84905e1158cb162b
Source dataset
uspto-grants-1995_05
Patent number
US05416235

Linked notes

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