Hydrochloric Acid → HCID 18426860, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (0.67 mL, 4.8 mmol) in tetrahydrofuran (6 mL) was added n-butyllithium (1.6 mol/L in hexanes; 2.7 mL, 4.3 mmol) at 0° C. under nitrogen atmosphere, and the reaction mixture was cooled to −78° C. 2-(4-Bromothiophen-2-yl)-5,6-dichlorobenzimidazole (500 mg, 1.44 mmol) in tetrahydrofuran (14 mL) was added dropwise followed by the addition of dimethylformamide (0.33 mL, 4.3 mmol), and the mixture was stirred for 30 min. Water and hydrochloric acid (1 mol/L) were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was triturated with ethyl acetate to afford 2-(3-bromo-2-formylthiophen-5-yl)-5,6-dichlorobenzimidazole (296 mg, 55%).

Provenance & Evidence