Dimethylformamide → 2-Bromo-6-chlorobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

A 1.6 molar solution of butyllithium in hexanes was placed in a three-neck flask equipped with a stirrer, addition funnel, low-temperature thermometer and nitrogen inlet tube at 0° C. A solution of diisopropyl amine in anhydrous tetrahydrofuran was added dropwise. The resulting solution was stirred at 0° C. for ten minutes, then cooled to −78° C. Upon cooling, a solution of 1-bromo-3-chlorobenzene in anhydrous tetrahydrofuran was added dropwise. The reaction was stirred at −78° C. for one hour. Anhydrous dimethylformamide was added. The solution was allowed to slowly warm to room temperature, followed by the addition of acetic acid and water. The aqueous mixture was extracted with ether twice and the ether layers were separated. The combined ether layers were successively washed with aqueous hydrochloric acid and brine. The separated organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel, eluting with hexanes-ethyl acetate to yield 2-chloro-6-bromobenzaldehyde.

Provenance & Evidence