Sodium Cyanide → Methyl 4-(cyanomethyl)-3-fluorobenzoate

HRID 410038Notes

Reaction equation

HRID 410038 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[F:13].[C-:14]#[N:15].[Na+]>CO.O>[C:14]([CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[F:13])#[N:15]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 18766370Methyl 4-(bromomethyl)-3-fluorobenzoate

Product 1

HCID 53684460Methyl 4-(cyanomethyl)-3-fluorobenzoateYield 63.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of methyl 4-(bromomethyl)-3-fluorobenzoate (18 g, 73 mmol) in MeOH (150 ml) was added the solution of NaCN (7.2 g, 146 mmol) in H2O (40 ml). The mixture was stirred at 65° C. for 5 hours. Most of MeOH was evaporated and additional water was added and extracted by EtOAc (200 ml×3), dried with anhydrous Na2SO4, filtered and evaporated to give the crude product. Purification by column chromatography (PE/EtOAc=50/1 to 10/1) gave the product (8 g, 63.8%).

Workup

  1. customMost of MeOH was evaporated
  2. additionadditional water was added
  3. extractionextracted by EtOAc (200 ml×3)
  4. dry with materialdried with anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product
  8. customPurification by column chromatography (PE/EtOAc=50/1 to 10/1)

Sources & evidence

ORD record
ord-dfa649f956484387a1d832356ecdfe0e
Source dataset
uspto-grants-2014_06
Patent number
US08759548B2

Reaction notes

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