Dichloromethane → 4-[(2-Bromo-8-fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol

Participants

Reaction Steps

8-Fluoro-5-(4-methoxyphenylsulfonyl)-6-methyl-5,6-dihydrophenanthridine (0.64 g, 1.7 mmol) was treated with 1 M boron tribromide in dichloromethane (6.6 mL, 6.6 mmol) and stirred at room temperature for twelve hours. A solution of saturated, aqueous, sodium bicarbonate (50 mL) was added slowly to the reaction, followed by extraction of the mixture with dichloromethane (6×20 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to a crude material. The crude material was filtered through a short column of silica gel, eluted with a mixture of ethyl acetate-hexane (1:4), and the filtrate concentrated in vacuo to a solid. After trituration with dichloromethane and filtration, the title compound was obtained as a homogeneous solid (0.23 g, 37%), m.p. 237-239° C.;

Provenance & Evidence