Dichloromethane → HCID 10317801, compound

Participants

Reaction Steps

A mixture of 8-fluoro-5-[(4-methoxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.30 g, 0.75 mmol) and tetrabutylammonium iodide (0.69 g, 1.9 mmol) was treated with 1 M boron trichloride in dichloromethane (1.9 mL, 1.9 mmol) at room temperature. After stirring for 24 hours at room temperature, the mixture was treated sequentially with water (20 mL), a saturated, aqueous, sodium bicarbonate solution (50 mL), and ether (20 mL). The separated aqueous phase was extracted with diethyl ether (3×25 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to a residue. The residue was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:4 to 3:7 gradient) to yield, the title compound as a homogeneous solid (0.21 g, 73%), m.p. 196° C.;

Provenance & Evidence