Toluene → 4-(bromoacetyl)-7-methyl-2H-chromen-2-one

Reaktionsgleichung

C([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([CH3:16])=[CH:13][CH:14]=2)[O:9][C:8](=[O:17])[CH:7]=1)=[CH2:5])C.[Br:18]N1C(=O)CCC1=O.C1(C)C=CC=CC=1>C1COCC1.O>[Br:18][CH2:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([CH3:16])=[CH:13][CH:14]=2)[O:9][C:8](=[O:17])[CH:7]=1)=[O:5]

Komponenten

Versuchsvorschrift

To a solution of 4-(1-ethoxyvinyl)-7-methyl-2H-chromen-2-one (1.56 g, 6.77 mmol) in THF-water (27.5 mL, 10/1 mixture), N-bromosuccinimide (1.33 g, 7.45 mmol) was added. The reaction was then stirred at room temperature. After 3 hours stirring, toluene was added and the crude mixture was evaporated under reduced pressure. The crude residue obtained was purified by column chromatography (EtOAc/hexanes, 30:70) to afford the title compound. 1H NMR (400 MHz, acetone-d6): 7.71 (d, 1H), 7.24 (s, 1H), 7.22 (d, 1H), 6.94 (s, 1H), 4.90 (s, 2H), 2.50 (s, 3H).