Acetonitrile → Methyl 3-(cyanomethyl)benzoate

HRID 1800402Notes

Reaction equation

HRID 1800402 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C-]#N.[K+].[C:15](#[N:17])[CH3:16]>C1OCCOCCOCCOCCOCCOC1>[C:15]([CH2:16][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])#[N:17]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 9032Potassium CyanideHCID 12070Methyl 3-bromobenzoate

Product 1

HCID 10821136Methyl 3-(cyanomethyl)benzoateYield 91%

Reagents, catalysts & solvents 1

HCID 2855718-Crown-6Catalyst

Procedure

To a solution of methyl 3-bromobenzoate (10.0 g, 44 mmol) in acetonitrile (100 mL) were added potassium cyanide (5.7 g, 87 mmol) and 18-crown-6 (1.0 g), and the mixture was stirred at room temperature for 3 days. The reaction mixture was filtrated, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→30/70). The combined solution was concentrated under reduced pressure to give the title compound (7.0 g, 91%) as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. customthe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→30/70)
  4. concentrationThe combined solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fcd6d9945d834c4c9f967341ba96a540
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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