Toluene → 4-(1,3-Thiazol-2-yl)benzaldehyde

Participants

Reaction Steps

A mixture of 2-bromothiazole (0.9 ml, 10 mmols), 4-formylphenylboronic acid (1.65 g, 11 mmols), sodium carbonate (2.65 g, 25 mmols), toluene (150 ml), ethanol (30 ml) and water (30 ml) was stirred in an argon atmosphere at room temperature for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.58 mg, 0.5 mmols) was added thereto and heated under reflux for 15 hours. The reaction-mixture was cooled, poured into water, and extracted with ethyl acetate. The extract was washed with water and brine, then dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography, and then recrystallized from ethyl acetate/hexane to give 4-(2-thiazolyl)benzaldehyde (1.4 g, 74%).

Provenance & Evidence