Sulfuric Acid → 2,6-Dibromobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To anhydrous THF (70 ml), diisopropylamine (8.3 ml, 59.34 mmol) was added and then n-BuLi (1.6 M, 59.34 mmol) was slowly added dropwise at 0° C. using a syringe in a nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 30 min, and the temperature thereof was cooled to −78° C. Subsequently, 1,3-dibromobenzene (7 g, 29.67 mmol) in THF (35 ml) was slowly added using a dropping funnel. The reaction mixture was stirred at −78° C. for 30 min, following the slow addition of DMF (4.6 ml, 59.34 mmol), and then continuously stirred for 1 hour. After the termination of the reaction, an aqueous solution of dilute H2SO4 was added, and the resulting solution was extracted two times with ethyl acetate, washed with a saturated NaCl solution, dried over anhydrous MgSO4, and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=40:1), thus obtaining the title compound as a white solid (6.64 g, 25.16 mmol, 85%).

Provenance & Evidence