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

HRID 367013Notes

Reaction equation

HRID 367013 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#N)[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 178418260HCID 178418260, compound

Product 1

HCID 18417526Methyl 3-cyano-2,4,5-trifluoro-benzoateYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

269 g of methyl 3-bromo-2,4,5-trifluoro-benzoate and 108 g of copper cyanide are heated to reflux for 5 hours in 400 ml of dimethylformamide. All volatile constituents of the reaction mixture are then removed by distillation in vacuo. The distillate is then fractionated on a column. 133 g of methyl 3-cyano-2,4,5-trifluoro-benzoate of boiling point 88-89° C./0.01 mbar are obtained.

Workup

  1. customAll volatile constituents of the reaction mixture are then removed by distillation in vacuo

Sources & evidence

ORD record
ord-d705c77f39044b13bb017887475eccd2
Source dataset
uspto-grants-2000_10
Patent number
US06133260

Reaction notes

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