[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]=C)=[CH:6][C:3]=1[C:4]#[N:5].I([O-])(=O)(=O)=[O:14].[Na+].[OH2:19]>C(Cl)(Cl)(Cl)Cl.C(#N)C.C(Cl)Cl.O.[Ru]=O>[C:4]([C:3]1[CH:6]=[C:7]([CH2:10][C:11]([OH:14])=[O:19])[CH:8]=[CH:9][C:2]=1[F:1])#[N:5]
A stirred solution of 2-fluoro-5-(prop-2-en-1-yl)benzonitrile (1.9 g, 11.8 mmol) in CCl4 (25 mL), acetonitrile (25 mL) and water (38 mL) was added sodium periodate (8.83 g, 41.3 mmol) and ruthenium oxide hydrate (200 mg) and the resulting mixture was stirred at ambient temperature overnight. The mixture was diluted with 100 mL DCM and 100 mL of water. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified with silica gel column chromatography afford crude (3-cyano-4-fluorophenyl)acetic acid.
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