Sodium Cyanide → Methyl 4-(cyanomethyl)benzoate

HRID 1716842Notes

Reaction equation

HRID 1716842 reaction equation
[C-:1]#[N:2].[Na+].Br[CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1>CS(C)=O>[C:1]([CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)#[N:2]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 848548Methyl 4-(cyanomethyl)benzoateYield 55%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of sodium cyanide (20 g, 0.41 mol) in dimethylsulfoxide at 40° C. was treated dropwise with a solution of methyl 4-(bromomethyl)benzoate (52 g, 0.227 mol) in dimethylsulfoxide, stirred for 90 min., cooled to room temperature, quenched with saturated aqueous sodium chloride and extracted with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. Purification of the concentrate via column chromatography (silica, hexanes:ethyl acetate 0→5%) provided methyl 4-(cyanomethyl)benzoate (55%). 1H NMR (400 MHz, CDCl3): 8.05 (d, J=8 Hz, 2H); 7.42 (d, J=8 Hz, 2H); 3.93 (s, 3H); 3.81 (s, 2H). [M+H] 176

Workup

  1. customquenched with saturated aqueous sodium chloride
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the
  7. concentrationconcentrate via column chromatography (silica, hexanes:ethyl acetate 0→5%)

Sources & evidence

ORD record
ord-82de8496fdf04423b7ea56af86475585
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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