4-Bromobenzoyl chloride → HCID 21182619, compound

Participants

Reaction Steps

To a solution of 1-[2-[4-(benzo[b]thiophen-2-yl)phenoxy]ethyl]pyrrolidine (650 mg, 2.0 mmol) and 4-bromobenzoyl chloride (657 mg, 1.5 equiv) in dichloromethane (25 mL) at 0° C. in dark was added TiCl4 (1.0 mL, neat) slowly under argon. The resulting mixture was stirred at ambient temperature for 4 h before being transferred carefully to a stirring solution of saturated aqueous NaHCO3 (100 mL). After stirring for 30 min, the mixture was extracted with CH2Cl2 (3×100 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Chromatography with Et3N:MeOH:EtOAc (4:4:92) afforded the product (940 mg, 92%).

Provenance & Evidence