[Cl:1][C:2]1[C:13]([Cl:14])=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[C:4]([F:15])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1.O>[Cl:1][C:2]1[C:13]([Cl:14])=[CH:12][C:5]([CH:6]=[O:7])=[C:4]([F:15])[CH:3]=1To a stirring solution of 4,5-dichloro-2-fluoro-N-methoxy-N-methyl-benzamide (5.1 g, 20.23 mmol) in THF (100 mL) at −78° was added a solution of lithium aluminum hydride in THF (12.14 mL of 2 M, 24.28 mmol). After 3 h at −78° C., 50 mL water was added followed by 50 mL of 1N HCl. The reaction was allowed to warm to 25° C. and stirred for 1 h. The reaction was diluted with water and extracted with diethyl ether. The ether was dried over Na2SO4, filtered, and concentrated to provide crude 4,5-dichloro-2-fluoro-benzaldehyde that was taken directly into the next step without further purification.
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