Boron trifluoride etherate → DipyrroMetheneboron Difluoride

Participants

Reaction Steps

2-[(3,5-Dimethyl-2H-pyrrol-2-ylidene)methyl]-3,5-dimethyl-1H-pyrrole monohydrochloride (4 g, 16.89 mmol) was dissolved into 125 ml of dry dichloromethane to which triethylamine (17.09 g, 168.9 mmol) was added and allowed to stir for 15 minutes. The solution was then cooled with an ice bath to control the temperature during the slow addition of boron trifluoride etherate (2185 g, 168.9 mmol). Once the addition was complete, the ice bath was removed and the reaction was allowed to stir at room temperature for 2 hours. The reaction was then quenched with water and extracted three times with dichloromethane. The organic layer was then washed with saturated sodium carbonate. The organic layer was impregnated onto silica gel and then purified via column chromatography (10% dichloromethane in hexanes) to yield 3.44 g of Bodipy (82% yield).

Provenance & Evidence