[Br:1][C:2]1[C:9]([OH:10])=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:11])[CH:3]=1.[CH2:12](Cl)[O:13][CH3:14].[H-].[Na+].CCOCC>CN(C)C=O>[Br:1][C:2]1[C:9]([O:10][CH2:12][O:13][CH3:14])=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:11])[CH:3]=14-Bromo-2-fluoro-5-hydroxy-benzaldehyde (750 mg, 3.41 mmol) and MOMCl (545 mg, 6.82 mmol) were dissolved in anhydrous N,N-dimethylformamide (5 mL) and cooled to 0° C. NaH (160 mg, 60% suspension in mineral oil, 4 mmol) is then added. The resulting mixture is allowed to stir at room temperature for 1 h. Ether is then added and washed with H2O (3×20 mL) and brine. After dried over Na2SO4, the ether is removed and the residue is purified through chromatography to afford the desired MOM ether (700 mg, 78%).
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