Methyl iodide → methyl 3-fluoro-2-formylbenzoate

Reaction equation

[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]([OH:12])[O:5][C:6]2=[O:7].[C:13](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[F:1][C:2]1[C:3]([CH:4]=[O:12])=[C:8]([CH:9]=[CH:10][CH:11]=1)[C:6]([O:5][CH3:13])=[O:7]

Participants

Procedure

A stirred mixture containing 7.36 g 4-fluoro-3-hydroxyphthalide, 18.15 g potassium carbonate and 11 mL methyl iodide in 125 mL acetone is heated at reflux for two hours. After stirring overnight at room temperature, the mixture is filtered and concentrated. The residue is dispersed in 200 mL ether, filtered and the filtrate concentrated to give 7.6 g residue which is used directly without further purification. The nmr spectrum of this material is consistent with that expected for the desired product.