Diethyl Ether → (4-Bromophenyl)(cyclohexyl)methanol

Participants

Reaction Steps

A solution of 4-bromobenzaldehyde (4.5 g, 24.32 mmol) in THF (40 ml) was immersed in an ice/methanol bath, followed by the dropwise addition of cyclohexylmagnesium chloride (2M) in diethylether (18.24 ml, 36.5 mmol) at −1° C. to +2° C. The reaction was allowed to warm up to room temperature and the reaction was stopped after 1 hr. The reaction mixture was quenched with saturated aqueous NH4Cl solution before dilution with ethyl acetate. The organic phase was separated and washed with brine. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo to obtain the crude product which was purified by flash chromatography (normal phase, n-heptane (isom. mixture)/ethyl acetate 4:1) to obtain the title compound as yellow oil.

Provenance & Evidence