Boron tribromide → 4-[2-(3-Nonyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol

Participants

Reaction Conditions

Reaction Steps

To a cooled solution of 0.06 mL of boron tribromide (0.6 mmol) in 2 mL dichloromethane, 5-[2-(3,4-dimethoxy-phenyl)-vinyl]-3-nonyl-[1,2,4]oxadiazole (compound of Example 33; 0.1 g, 0.27 mmol) dissolved in 8 mL of dichloromethane was added over a period of 15-20 min at −45° C. to −40° C. The reaction mixture was stirred at −45 to −40° C. for 15-20 min and allowed to attain a temperature of 25° C. to 30° C. over a period of 1 h. The reaction mixture was further stirred at 25° C. to 30° C. for 4-5 h. After the completion of the reaction, the reaction mixture was quenched in 20 mL of chilled 5% sodium bicarbonate solution at a temperature below 20° C. (pH 8-9). 10 mL of ethyl acetate was added to the reaction mixture to dissolve the solid and stirred for 10-15 min. The organic layer was separated and the aqueous layer was washed with 10 mL of 10% sodium chloride solution. The organic layer was collected and distilled to obtain a crude material, which was purified by column chromatography (silica gel, chloroform-methanol) to yield the title compound.

Provenance & Evidence