Thionyl Chloride → 8-bromooctanoyl Chloride

Participants

Reaction Steps

To 8-bromooctanoic acid (2.5 g, 11.2 mmol, commercially available e.g. from Aldrich) in toluene (50 ml) was added thionyl chloride (2 ml), and the mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was co-evaporated with dichloromethane (2×25 ml) to give a brown oil which solidified on standing (found to be starting acid by NMR). This material was redissolved in toluene (25 ml), thionyl chloride (2 ml) was added, and the mixture was stirred at room temperature for 8 hours and then left standing overnight. The reaction mixture was evaporated to dryness and the residue was co-evaporated with dichloromethane (2×30 ml) to give the title compound as a brown oil (2.4 g), as a 3:2 mixture of product: starting acid (by NMR). 1H NMR (400 MHz, chloroform-d) δ (delta) ppm 1.37 (4H, m), 1.45 (2H, m), 1.67 (2H, m), 1.86 (2H, m), 2.90 (2H, t, J=7 Hz), 3.42 (2H, t, J=7 Hz).

Provenance & Evidence