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

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Reaction Steps

A stirred suspension of 6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-2-phenyl-5,6-dihydrophenanthridine (0.13 g, 0.26 mmol) and cyclohexene (0.48 mL, 4.8 mmol) was treated drop-wise at room temperature under nitrogen with a solution of 1 M boron tribromide in dichloromethane (1.6 mL, 1.6 mmol). After stirring for 20 hours at room temperature, the reaction was quenched by the drop-wise addition of a saturated, aqueous, sodium bicarbonate solution (300 mL), followed by extraction with dichloromethane (6×20 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to a crude product. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:4 to 3:7 gradient), followed by re-crystallization from a mixture of ethyl acetate-hexane, to yield 4-[(6-ethyl-8-fluoro-2-phenylphenanthridin-5(6H)-yl)sulfonyl]phenol as a homogeneous solid (0.09 g, 71%), m.p. 207° C.;

Provenance & Evidence