N-Fluorobenzenesulfonimide → HCID 66914960, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (2.06 mL, 1.6M solution, 3.30 mmol) was added to a solution of 3-bromo-1,2-dimethyl-4-phenyl-pyrrole (550 mg, 2.20 mmol) in tetrahydrofuran (10 mL) at −78° C. and the reaction mixture was stirred at −78° C. for 30 min. A solution of n-fluorodibenzene sulfonamide (901 mg, 2.86 mmol) in tetrahydrofuran (8 mL) was added to the reaction mixture at −78° C. and the reaction mixture was stirred at this temperature for another 1 h. The reaction mixture was allowed to warm to ambient temperature and stirred for 16 h after which time the reaction mixture was quenched with dilute HCl and evaporated to dryness. The residue was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. Purification by preparative HPLC afforded 3-fluoro-1,2-dimethyl-4-phenyl-pyrrole (160 mg, 39%) as a solid.

Provenance & Evidence