Potassium Cyanide → Methyl 3-(cyanomethyl)benzoate

HRID 2180238Notes

Reaction equation

HRID 2180238 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[C-:13]#[N:14].[K+]>CS(C)=O>[C:13]([CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])#[N:14]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 10821136Methyl 3-(cyanomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of methyl 3-(bromomethyl)benzoate (2.29 g, 0.01 mol) and potassium cyanide (3.26 g, 0.05 mol) in DMSO (20 mL) was heated to 100° C. for 1 h. The reaction mixture was cooled, partitioned between ether and water, washed with brine, dried (Na2SO4) and concentrated to give the title compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between ether and water
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0002a93fec8f4387b3c67b376ff03867
Source dataset
uspto-grants-2005_05
Patent number
US06887863B2

Reaction notes

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