4-Bromobenzaldehyde → 1-(4-Bromophenyl)-2-methylpropan-1-ol

Reaction equation

[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].C(=O)(O)[O-].[Na+]>CCOCC>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([CH:10]([CH3:12])[CH3:11])[OH:7])=[CH:4][CH:3]=1

Participants

Procedure

To a solution of 9.0 g (0.048 mol) of 4-Bromobenzaldehyde in 150 mL of ether at 0° C. under argon, 2.0 M solution of isopropyl magnesium chloride in ether (29.2 mL) was added and stirred for 30 minutes. The solution was slowly warmed up to room temperature and stirred for an additional 4 hours. The mixture was then added to 150 mL of aqueous saturated sodium bicarbonate and extracted with 200 mL of ether. The organic extract was washed once with water, dried and evaporated to afford 9.8 g (95%) of the product as a gum.