Ethyl acetate hexane → Methyl 2-cyano-3-fluoro-6-methylbenzoate

HRID 333220Notes

Reaction equation

HRID 333220 reaction equation
[F:1][C:2]1[C:3](I)=[C:4]([C:9]([CH3:12])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Cu][C:15]#[N:16].CCCCCC.C(OCC)(=O)C>CN(C)C=O>[C:15]([C:3]1[C:2]([F:1])=[CH:11][CH:10]=[C:9]([CH3:12])[C:4]=1[C:5]([O:7][CH3:8])=[O:6])#[N:16]

Participants

5

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 67192788Benzoic acid, 3-fluoro-2-iodo-6-methyl-, methyl esterHCID 178418546HCID 178418546, compound

Product 1

HCID 67192265Methyl 2-cyano-3-fluoro-6-methylbenzoateYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-fluoro-2-iodo-6-methylbenzoate (440 mg, 1.49 mmol) and copper(I) cyanide (200 mg, 2.24 mmol) were dissolved in N,N-dimethylformamide (5.5 mL) and the resulted solution was refluxed under nitrogen atmosphere for 3 hours. The solvent was removed under reduced pressure and the residue was diluted with dichloromethane and washed with 15% ammonium hydroxide. Organic phase was dried over sodium sulfate, filtered and evaporated. Column chromatography (n-hexane/ethyl acetate: 7/3) afforded title compound (210 mg, 73% yield).

Workup

  1. temperaturethe resulted solution was refluxed under nitrogen atmosphere for 3 hours
  2. customThe solvent was removed under reduced pressure
  3. additionthe residue was diluted with dichloromethane
  4. washwashed with 15% ammonium hydroxide
  5. dry with materialOrganic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d275c48802534ce3835731cb5ede52f2
Source dataset
uspto-grants-2014_11
Patent number
US08877944B2

Reaction notes

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