Thionyl Chloride → 4-{4-[(4-Bromobutyl)oxy]butyl}benzoyl chloride

Participants

Reaction Steps

A suspension of 4-{4-[(4-bromobutyl)oxy]butyl}benzoic acid (0.91 g, 2.77 mmol, e.g. which can be as prepared in Intermediate 25) in thionyl chloride (SOCl2, 2 ml) was stirred at room temperature for 1 hour and then at 100° C. for 2 hours. The reaction mixture was cooled and the excess thionyl chloride was removed by evaporation, followed by co-evaporation with dichloromethane (2×30 ml) to give the title compound as a brown oil (1.03 g). 1H NMR (400 MHz, chloroform-d) δ (delta) ppm 1.5-2.0 (10H, m); 2.75 (2H, m); 3.45 (4H, m); 7.35 (2H, d); 8.05 (2H, d). The compound was not pure by 1H NMR (CDCl3), but it was not purified further.

Provenance & Evidence