Sodium Cyanide → Methyl 2-(cyanomethyl)-3-fluorobenzoate
Reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[CH2:11]Br.[C-:14]#[N:15].[Na+]>CO>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[CH2:11][C:14]#[N:15]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
2-Bromomethyl-3-fluoro-benzoic acid methyl ester (5.1 g, 21 mmol) was dissolved in methanol (50 ml), and sodium cyanide aqueous solution (4.2 ml, 5 ml, 21 mmol) was added dropwise thereto. After completion of the dropwise addition, the mixture was stirred at 50° C. for 2 hours. The residue obtained by evaporating the solvent from the reaction solution under a reduced pressure was mixed with ethyl acetate, washed with water and saturated brine and then dried with anhydrous it magnesium sulfate. The solvent was removed by evaporation from the organic layer under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 3.3 g (17 mmol, 82% in yield) of the title compound.
Workup
- additionAfter completion of the dropwise addition
- customThe residue obtained
- customby evaporating the solvent from the reaction solution under a reduced pressure
- additionwas mixed with ethyl acetate
- washwashed with water and saturated brine
- dry with materialdried with anhydrous it magnesium sulfate
- customThe solvent was removed by evaporation from the organic layer under a reduced pressure
- customthe thus obtained material was separated
- custompurified by a silica gel column chromatography
- customto obtain
Sources & evidence
- ORD record
- ord-9d4d07d1cf2a409885662fb070ba81be
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06498251B1
Reaction notes
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