Sodium Cyanide → Methyl 3-(cyanomethyl)benzoate

HRID 1598808Notes

Reaction equation

HRID 1598808 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].[Na+]>CN(C=O)C.CCOC(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

5

Reactant 2

HCID 8929Sodium CyanideHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 10821136Methyl 3-(cyanomethyl)benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3-(bromomethyl)benzoate (8.5 g, 37 mmol) and sodium cyanide (1,8 g, 37 mmol) were stirred at room temperature in DMF (40 mL) overnight. The mixture was diluted with EtOAc and extracted several times with water containing a small amount of brine, then brine, dried (MgSO4), and solvent removed in vacuo. The crude product (6.8 g, yellow oil) was sufficiently pure to be used in the next step without purification. IR(neat): cm-1 2249, 1722. 1H-NMR(300 MHz, CDCl3): 8.03-8.01 (m, 2H), 7.57-7.46 (m, 2H), 3.94 (s, 3H), 3.82 (s, 2H).

Workup

  1. extractionextracted several times with water containing a small amount of brine
  2. dry with materialbrine, dried (MgSO4), and solvent
  3. customremoved in vacuo
  4. customto be used in the next step without purification

Sources & evidence

ORD record
ord-8414444f4a9c419fa1edf7d2b787fcaa
Source dataset
uspto-grants-1998_04
Patent number
US05739163

Reaction notes

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