4-Bromobenzaldehyde → 1-(4-Bromophenyl)hexan-1-ol

Participants

Reaction Steps

n-Pentylmagnesium bromide (12.1 mL of a 2.0 M solution in Et2O, 24.0 mmol) was added to a solution of 4-bromobenzaldehyde 5 (4.0 g, 22.0 mmol) at −78° C. The reaction was then warmed to room temperature for 0.5 h and quenched with saturated aqueous NH4Cl. The mixture was extracted with EtOAc and the organic portion was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. FCC (silica gel, 9:1 hex/EtOAc) gave 3.6 g (63%) of the alcohol 6 as a clear, colorless oil.

Provenance & Evidence