Water → 1H-Pyrrole, 2-[3,5-bis(trifluoromethyl)phenyl]-

Participants

Reaction Conditions

Reaction Steps

A 500 mL 3-neck round-bottomed flask was charged with a solution of pyrrole (5.15 g, 76.79 mmol) in THF (120 mL) at rt and cooled to 0° C. NaH(2.21 g, 92.12 mmol) was added portionwise and the reaction mixture was stirred at 0° C. for 1 h. To this reaction mixture, ZnCl2 (10.4 g, 77 mmol) was added and stirred at 0° C. for 1 h. 1-Bromo-3,5-bis(trifluoromethyl)benzene (5.0 g, 17.0 mmol) was added and reaction was properly degassed for 10 min and palladium diacetate (0.172 g, 0.76 mmol) and 2-(dicyclohexyl phosphino)biphenyl (0.269 g, 0.76 mmol) were added and reaction was refluxed for 48 h. Reaction mixture was transferred into water (100 mL) and extracted with EtOAc (3×300 mL) and the combined organic layers were washed with saturated brine solution (3×150 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to afford 7 g of crude 2-(3,5-bis(trifluoromethyl)phenyl)-1H-pyrrole which was purified by chromatography to afford 0.8 g of pure product. LCMS calcd for: C12H6F6N [M−H]− 278.18. found 278.19 (retention time 3.383 min)

Provenance & Evidence