Dimethyl Sulfoxide → trans-2-(4-Bromophenyl)cyclopropane-1-carbaldehyde

Participants

Reaction Steps

DMSO (3 equivalents) was added dropwise to a solution of oxalyl chloride in anhydrous dichloromethane under N2 at −78° C. A solution of the alcohol from Example 28B ((1S,2S)-[2-(4-bromophenyl)cyclopropyl]methanol) in dichloromethane was then added dropwise at −78° C. Stirring at this temperature was continued for 30 minutes, then triethylamine (4 equivalents) was added and the dry ice bath was removed. After stirring for 1 hour, the mixture was treated with saturated aqueous NH4Cl. The mixture was extracted with ether. The combined organic extracts was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by eluting through a pad of silica gel with hexane to provide the title compound.

Provenance & Evidence