F[C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8].[CH2:13]([OH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:13]([O:20][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1A mixture of 5-fluoro-2-nitrobenzonitrile (15 g, 90 mmol), benzyl alcohol (10.8 g, 100 mmol) and potassium carbonate (18.7 g, 135 mmol) in DMF (20 ml) was stirred at room temperature for 60 h. Water (60 ml) was added to the reaction, and the resultant yellow precipitate out filtered, washed with water, and dried under reduced pressure to provide 17.3 g (75.4%) of 5-benzyloxy-2-nitrobenzonitrile. The compound was used directly for the next step without further purification. MS GC-MS M+=211, RT=6.15 min.
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