Water → Methyl 4-cyano-2-fluorobenzoate

HRID 2170953Notes

Reaction equation

HRID 2170953 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([F:12])[CH:4]=1)#[N:2].[C:13](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.O>CC(C)=O>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:13])=[O:8])=[C:5]([F:12])[CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 5906594-Cyano-2-fluorobenzoic acid

Product 1

HCID 15278726Methyl 4-cyano-2-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

13.20 g (79.9 mmol) of 4-cyano-2-fluorobenzoic acid are dissolved in 300 ml of acetone. Then 22.10 g (159.9 mmol) of potassium carbonate and 9.08 ml (95.9 mmol) of dimethyl sulfate are successively added. The mixture is stirred at reflux temperature for 20 h. The reaction mixture is then mixed with 300 ml of water and the acetone is removed in a rotary evaporator. Several extractions with dichloromethane are carried out. The combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulfate. The solvent is then removed in vacuo. The remaining solid is used further without further purification. 16.1 g (84% of theory) of the title compound are obtained as a colorless solid.

Workup

  1. temperatureat reflux temperature for 20 h
  2. customthe acetone is removed in a rotary evaporator
  3. extractionSeveral extractions with dichloromethane
  4. washThe combined organic phases are washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is then removed in vacuo
  7. customThe remaining solid is used further without further purification

Sources & evidence

ORD record
ord-662b3aa321c44e92ac88b9e5a95d3252
Source dataset
uspto-grants-2015_06
Patent number
US09051316B2

Reaction notes

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