Boron tribromide → Scutellarein

Participants

Reaction Steps

Boron tribromide (0.7 mL) was added dropwise to a solution of the flavone 1c (68.4 mg, 0.2 mmol) in dichloromethane (3 mL) at 0° C. The mixture was allowed to warm to room temperature after 30 min and stirred at room temperature for 20 h. Then the mixture was poured into ice water (20 mL). The organic layer was separated and concentrated under reduce pressure. The aqueous layer was poured onto the organic residue. After stirring, the precipitate was filtered off and washed with water. Recrystallization from ethanol afforded the title compound (50 mg, 88%) as yellow crystals: 1H NMR (DMSO, 200 M Hz) δ 10.20 (br s, 2H), 7.90 (d, J=8.7 Hz, 2H), 6.90 (d, J=8.7 Hz, 2H), 6.72 (s 1H), 6.57 (s 1H), 3.75 (br s, 2H)); 13C NMR (DMSO, 50 M Hz) δ 182.1 (s), 163.6 (s), 161.0 (s), 153.3 (s), 149.7 (s), 147.1 (s), 129.2 (s), 128.4 (d, 2C), 121.5 (s), 116.0 (d, 2C), 104.1 (s), 102.3 (d), 93.9 (d).

Provenance & Evidence