Nitric Acid → 2-Chloro-4-fluoro-5-nitrobenzyl cyanide

HRID 1709776Notes

Reaction equation

HRID 1709776 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[CH2:4][C:5]#[N:6].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[CH2:4][C:5]#[N:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 27250632-Chloro-4-fluorophenylacetonitrile

Product 1

HCID 230367452-Chloro-4-fluoro-5-nitrobenzyl cyanide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

10 g of 2-chloro-4-fluorobenzyl cyanide are dissolved at a temperature of -10° C., with stirring, in 85 ml of concentrated sulfuric acid, in the process of which a fine light-brown suspension is formed. There are then slowly added dropwise at -20° C., with stirring, 5 ml of fuming nitric acid. After completion of the addition, stirring is continued for a further half hour, the temperature rising to 0° C. The reaction mixture is poured onto 500 g of ice, and the substance which precipitates is extracted with methylene chloride. The methylene chloride phase is dried over sodium sulfate, and concentrated by evaporation to leave 10.5 g of 2-chloro-4-fluoro-5nitrobenzyl cyanide in the form of white crystals having a melting point of 67°-68° C.

Workup

  1. customis formed
  2. additionThere are then slowly added dropwise at -20° C.
  3. additionAfter completion of the addition
  4. stirringstirring
  5. customrising to 0° C
  6. customthe substance which precipitates
  7. extractionis extracted with methylene chloride
  8. dry with materialThe methylene chloride phase is dried over sodium sulfate
  9. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-82c5f590ab0143d6becef0e95991aa86
Source dataset
uspto-grants-1990_08
Patent number
US04950777

Reaction notes

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