HCID 67325611, compound → HCID 67324020, compound

HRID 1397263Notes

Reaction equation

HRID 1397263 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][CH3:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Cu](C#N)[C:15]#[N:16]>CN(C=O)C>[C:15]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][CH3:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])#[N:16]

Participants

4

Reactant 2

HCID 67325611HCID 67325611, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 67324020HCID 67324020, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product methyl 3-bromo-5-ethylbenzoate (0.9 g, 3.7 mmol) was dissolved in dry DMF (50 mL) and copper cyanide (0.84 g, 9.43 mmol) was added. The reaction mixture was heated to 150° C. under argon atmosphere for 12 h (monitored by TLC; petroleum ether/EtOAc 9:1). The reaction mixture was allowed to come to room temperature and then quenched with saturated ammonium chloride solution. The reaction mixture was diluted with EtOAc and filtered through a Celite bed. The filtrate was diluted with EtOAc and the organic layer was washed with water and brine. The solvent was evaporated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluent 5% EtOAc in petroleum ether) to get methyl 3-cyano-5-ethylbenzoate (0.27 g, yield 39%) as colorless liquid, which was carried through without further purification.

Workup

  1. customto come to room temperature
  2. customquenched with saturated ammonium chloride solution
  3. additionThe reaction mixture was diluted with EtOAc
  4. filtrationfiltered through a Celite bed
  5. additionThe filtrate was diluted with EtOAc
  6. washthe organic layer was washed with water and brine
  7. customThe solvent was evaporated under reduced pressure
  8. customThe crude product was purified by column chromatography (silica 60-120 mesh, eluent 5% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-c200f8db42a84c4b8bd7b7787641c199
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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