ClC1[C:3](F)=[C:4](C(C)=CC=1)[CH:5]=[O:6].C[C:13]1([CH3:21])[CH2:18][CH2:17][CH2:16][C:15](C)(C)N1.[Li]CCCC.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][C:29]=1[F:35].C[N:37]([CH:39]=[O:40])C.C1C[O:44]CC1>O>[Cl:27][C:28]1[C:29]([F:35])=[C:30]([C@@H:3]([NH:37][C:39](=[O:40])[O:44][C:15]2[CH:16]=[CH:17][CH:18]=[CH:13][CH:21]=2)[CH2:4][CH:5]=[O:6])[C:31]([CH3:34])=[CH:32][CH:33]=13-Chloro-2-fluoro-6-methylbenzaldehyde: (Reference: E. J. Org. Chem 2005, 2116-2123) To a solution of 2,2,6,6-tetramethylpiperidine (0.642 mL, 3.80 mmol) in THF (15 mL) at −78° C. was added n-BuLi (2.162 mL, 3.46 mmol) dropwise. The resulting solution was stirred at −78° C. for 1 h and added 1-chloro-2-fluoro-4-methylbenzene (0.5 g, 3.46 mmol) dropwise. The solution was stirred for additional 0.5 h and then added DMF (0.536 mL, 6.92 mmol). The reaction was stirred at −78° C. for 1.5 h and at ambient temperature for 12 h. The mixture was diluted with water and extracted with EtOAc (3×). The combined organic layer was washed with brine and concentrated. The residue was purified by silica gel chromatography to yield the desired product (43 mg, 7%).
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