[C:1](=[O:4])([O-])[O-].[K+].[K+].IC.[F:9][C:10]1[C:11]([N+:19]([O-:21])=[O:20])=[CH:12][C:13](O)=[C:14]([CH:17]=1)[CH:15]=[O:16].O>CN(C)C=O>[F:9][C:10]1[C:11]([N+:19]([O-:21])=[O:20])=[CH:12][C:13]([O:4][CH3:1])=[C:14]([CH:17]=1)[CH:15]=[O:16]To a suspension of 0.524 g (3.80 mmole) of potassium carbonate, 0.5 mL of iodomethane and 8 mL of dimethylformamide was added, dropwise, a solution of 0.141 g (0.76 mmole) of 5-fluoro-2-hydroxy-4-nitro-benzaldehyde (IV.46b) in 1 mL of dimethylformamide. The resulting dark red solution was stirred at room temperature for 3 hours. The mixture was poured into 50 mL of water and extracted three times with 25 mL of ethyl acetate. The combined organic layers were washed three times with 25 mL of water, once with 25 mL of brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.143 g of 5-fluoro-2-methoxy-4-nitro-benzaldehyde (IV.46c) as a yellow solid.
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