[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]([Mg]Cl)([CH3:12])[CH3:11].[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1To a solution of 4-brombenzaldehyde (27 mmol, 5.0 g) in THF (20 mL) was added at −78° C. a solution of isopropylmagnesium chloride (41 mmol, 20.2 mL, 2M in ether). The mixture was stirred at −78° C. for 1 h and warmed to 0° C. for 1 h. NH4Cl was added an the mixture was extracted with EtOAc. The organic extract was washed with brine, dried and concentrated to an oil. Chromatography (5-15% EtOAc/hexane) gave the desired alcohol.
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