[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.C(NC(C)C)(C)C.[Li].[CH3:17][C:18]([CH3:20])=[O:19]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:8])[C:7]=1[C:18]([OH:19])([CH3:20])[CH3:17]To a round bottom flask is added 3-bromo-5-fluoropyridine (475 mg, 2.7 mmol) in 4 ml of dry THF at −78° C., followed by the addition of lithium diisopropylamine (1.6 ml, 3.2 mmol). The reaction mixture is stirred at −78° C. for 1 hour, followed by the addition of acetone (0.6 ml). The reaction mixture is warmed up and stirred at room temperature for 30 minutes. The reaction mixture is diluted with EtOAc, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude product. Purification by the flash column chromatography affords 190 mg of 2-(3-bromo-5-fluoro-pyridin-4-yl)-propan-2-ol.
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