Methyl 3-bromo-2,4,5-trifluorobenzoate → Methyl 3-cyano-2,4,5-trifluoro-benzoate

HRID 430591Notes

Reaction equation

HRID 430591 reaction equation
Br[C:2]1[C:3]([F:14])=[C:4]([CH:9]=[C:10]([F:13])[C:11]=1[F:12])[C:5]([O:7][CH3:8])=[O:6].[Cu][C:16]#[N:17]>CN(C)C=O>[C:16]([C:2]1[C:3]([F:14])=[C:4]([CH:9]=[C:10]([F:13])[C:11]=1[F:12])[C:5]([O:7][CH3:8])=[O:6])#[N:17]

Participants

4

Reactant 2

HCID 18459836Methyl 3-bromo-2,4,5-trifluorobenzoateHCID 178418546HCID 178418546, compound

Product 1

HCID 18417526Methyl 3-cyano-2,4,5-trifluoro-benzoateYield 61.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 269 g of methyl 3-bromo-2,4,5-trifluorobenzoate, 108 g of copper(I) cyanide and 400 ml of dimethylformamide is heated under reflux for 5 hours. All volatile components are distilled off in vacuo. Fractional distillation of the resulting mixture gives 133 g of the title compound.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 5 hours
  3. distillationAll volatile components are distilled off in vacuo
  4. distillationFractional distillation of the resulting mixture

Sources & evidence

ORD record
ord-88c4248f374b4852b39ecf0afe36429e
Source dataset
uspto-grants-2001_11
Patent number
US06323213B1

Reaction notes

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