Ethanol → Ethyl 2-chloro-4-(cyanomethyl)benzoate

HRID 411758Notes

Reaction equation

HRID 411758 reaction equation
Br[CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:5]([Cl:14])[CH:4]=1.[C-:15]#[N:16].[K+].C(O)C>O>[Cl:14][C:5]1[CH:4]=[C:3]([CH2:2][C:15]#[N:16])[CH:13]=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 9032Potassium CyanideHCID 14459378Ethyl 4-(bromomethyl)-2-chlorobenzoate

Product 1

HCID 18541412Ethyl 2-chloro-4-(cyanomethyl)benzoateYield 16%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3.1 g (11.2 mmol) of ethyl 4-(bromomethyl)-2-chlorobenzoate are added dropwise to a solution composed of 0.94 g (14.3 mmol) of potassium cyanide, 3.75 ml of water and 8.8 ml of ethanol, heated under reflux. After refluxing for 3 hours, the medium is poured over 200 ml of water, and extracted with ethyl acetate. The organic phase is washed with a dilute HCl solution and then with water saturated with NaCl. The oil obtained after concentration of the organic phase is purified by flash chromatography on silica (hexane-ethyl acetate 1:0 to 1:1 gradient). 0.4 g of a brown solid is obtained (Yield=16%).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. temperatureAfter refluxing for 3 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with a dilute HCl solution
  6. customThe oil obtained after concentration of the organic phase
  7. customis purified by flash chromatography on silica (hexane-ethyl acetate 1:0 to 1:1 gradient)

Sources & evidence

ORD record
ord-2e955d488e2f471292f90a26e57fe066
Source dataset
uspto-grants-2003_05
Patent number
US06559185B2

Reaction notes

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