Hydrochloric Acid → 3-Oxo-3-(2,3,4,5-tetrafluorophenyl)propanenitrile

HRID 1788975Notes

Reaction equation

HRID 1788975 reaction equation
[C:1]([C:3](=[C:8]([OH:19])[C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([F:17])[C:10]=1[F:18])C(OC)=O)#[N:2].[Na].Cl>O>[F:18][C:10]1[C:11]([F:17])=[C:12]([F:16])[C:13]([F:15])=[CH:14][C:9]=1[C:8]([CH2:3][C:1]#[N:2])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 76172599HCID 76172599, compound

Product 1

HCID 139117863-Oxo-3-(2,3,4,5-tetrafluorophenyl)propanenitrileYield 88.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 2-cyano-3-hydroxy-3-(2,3,4,5-tetrafluorophenyl)acrylate (75.1 g) is added to a solution of sodium hydroxyde (110 g) in water (1.1 liter) and the mixture is stirred at room temperature for 26 hours. To the reaction mixture is added ice (1.3 Kg) and conc. HCl. After 1 hour, the precipitate is filtered and washed with dil. HCl to yield 2-(2,3,4,5-tetrafluorobenzoyl)acetonitrile (52.7 g) as a light cream colored powder, m.p. 60°-61° C.

Workup

  1. waitAfter 1 hour
  2. filtrationthe precipitate is filtered
  3. washwashed with dil. HCl

Sources & evidence

ORD record
ord-70fee91471c449a7acd7cc2f16112696
Source dataset
uspto-grants-1987_08
Patent number
US04686221

Reaction notes

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