Acetyl chloride → Methyl 2-cyano-5-fluorobenzoate
Reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])#[N:2].[C:13](Cl)(=O)C>CO>[CH3:13][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:3]=1[C:1]#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred suspension of 16.0 g (96.9 mmol) 2-Cyano-5-fluoro-benzoic acid (Apollo) and 161 ml methanol were added 30.4 g (387.6 mmol) acetyl chloride drop wisely at 0° C. The reaction mixture was stirred over night, filtered and concentrated. The residue was diluted with dichloromethane, washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The residue was purified by column chromatography (hexane:ethylacetate). The desired product 21a was obtained in 86.0 yield (14.9 g; 83.3 mmol)