Dimethylformamide → 2-Fluoro-3-iodobenzaldehyde
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C(NC(C)C)(C)C.[Li]CCCC.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[I:20].CN([CH:24]=[O:25])C>C1COCC1.O.C(O)(=O)C>[F:13][C:14]1[C:15]([I:20])=[CH:16][CH:17]=[CH:18][C:19]=1[CH:24]=[O:25]C(NC(C)C)(C)C.[Li]CCCC.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[I:20].CN([CH:24]=[O:25])C>C1COCC1.O.C(O)(=O)C>[F:13][C:14]1[C:15]([I:20])=[CH:16][CH:17]=[CH:18][C:19]=1[CH:24]=[O:25]To a solution of diisopropylamine (10.42 mL, 74.36) in THF (135 mL) under N2 in an ice bath at 0-5° C. was added dropwise over 10 min n-BuLi (42.25 mL, 67.6 mmol) and stirred at this temperature for 10 min. Cooled the reaction mixture to −78° C. in a dry ice/acetone bath and dropwise added 1-fluoro-2-iodobenzene (7.88 mL, 67.6 mmol) over 5 min. Stirred at this temperature for 1 h, dropwise added DMF (6.26 mL, 74.36 mL) over 5 min, and stirred for 10 min. Added Acetic Acid (13.5 mL) followed by H2O and extracted with Et2O (2×). The combined organic solution was washed (0.1 N HCl then brine), dried (MgSO4), filtered and concentrated. The crude benzaldehyde (16.9 g) was taken onto the next step without purification. 1H NMR was consistent with structure.
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