Potassium Cyanide → Methyl [4-(cyanomethyl)phenyl]acetate

HRID 1612409Notes

Reaction equation

HRID 1612409 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11]Br)=[CH:7][CH:6]=1.[C-:14]#[N:15].[K+]>CN(C)C=O.O>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:14]#[N:15])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 11770640Methyl 2-(4-(bromomethyl)phenyl)acetate

Product 1

HCID 53857233Methyl [4-(cyanomethyl)phenyl]acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 15 in dimethylformamide (0.3 M) at room temperature under nitrogen was added potassium cyanide (1.2 eq). The reaction was stirred at room temperature overnight. The reaction was diluted with H2O then extracted with ethyl acetate (3×). The organic phases were combined, washed with saturated sodium bicarbonate (1×), brine (1×), dried over sodium sulfate, filtered and concentrated in vacuo to afford the product. (26%) 1H NMR (400 MHz, CDCl3) δ 7.30 (s, 4H), 3.74 (s, 2H), 3.70 (s, 3H) 3.64 (s, 2H).

Workup

  1. extractionthen extracted with ethyl acetate (3×)
  2. washwashed with saturated sodium bicarbonate (1×), brine (1×)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford the product

Sources & evidence

ORD record
ord-303ea336fc8e40edb1d1f8a537f47855
Source dataset
uspto-grants-2006_01
Patent number
US06992193B2

Reaction notes

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