Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)=[O:4].[N-:13]=[N+:14]=[N-:15].[Na+]>C1COCC1.O>[N:13]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)=[O:4])=[N+:14]=[N-:15]To a solution of 2-bromo-1-[3-(methyloxy)phenyl]ethanone (2.4 g, 10.5 mmol) in THF (80 mL) and water (20 mL) was added sodium azide (1.703 g, 26.2 mmol), and the reaction mixture was stirred at room temperature for 60 hours. Water (40 mL) was added, and the aqueous mixture was extracted with EtOAc (3×80 mL). The organics were dried (Na2SO4), filtered, and concentrated under reduced pressure to afford the title compound (1.87 g) as a brown oil. 1H NMR (400 MHz, CDCl3): δ 3.87 (s, 3H), 4.55 (s, 2H), 7.15-7.18 (m, 1H), 7.38-7.42 (m, 1H), 7.44-7.47 (m, 2H).
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