Thionyl Chloride → HCID 89533691, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.50 g (8.10 mmol; 1.0 eq) of 2-fluoro-3-nitrobenzoic acid and 16 ml of thionyl chloride was refluxed for 3 hours. The excess thionyl chloride was then concentrated and the residue was co-evaporated twice with toluene. The resulting acid chloride was taken up in 25 ml of dichloromethane. 1.27 g (8.10 mmol; 1.0 eq) of isopropyl (S)-pyrrolidine-2-carboxylate were added to this mixture cooled to 0° C. The reaction medium was stirred at 0° C. for 30 minutes and then at ambient temperature for 2 hours. The reaction medium was diluted and washed with a 1 M hydrochloric acid solution (100 ml) and then with a saturated sodium hydrogen carbonate solution (100 ml). The organic phase was dried over MgSO4, filtered and evaporated. 2.12 g of isopropyl (S)-1-(2-fluoro-3-nitrobenzoyl)pyrrolidine-2-carboxylate were obtained. Yield=81%.

Provenance & Evidence