Nitric Acid → 5-Bromo-8-nitro-3,4-dihydronaphthalen-1(2H)-one

반응식

[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][C:11]2=[O:16].[OH-].[Na+]>S(=O)(=O)(O)O>[Br:5][C:6]1[CH:15]=[CH:14][C:13]([N+:1]([O-:4])=[O:2])=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][C:11]2=[O:16]

참가 물질

실험 절차

To prepare this compound, 90% fuming nitric acid (0.115 gram, 0.165 mmol) was added to a solution of 5-bromo-3,4-dihydro-2H-naphthalen-1-one (0.34 g, 1.50 mmol) in 3 mL concentrated sulfuric acid at 0° C. After 45 minutes, the mixture was poured into ice, and 6 N aqueous sodium hydroxide (9 mL) was added very slowly. That mixture was extracted twice with EtOAc (40 mL each), and the two extracts were combined. The combined EtOAc extract was washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was subjected to flash chromatography (40% EtOAc/hexanes) and recrystallization (EtOAc/hexanes) to afford 0.15 g (38%) of 5-bromo-3,4-dihydro-8-nitro-2H-naphthalen-1-one. 1H NMR (500 MHz, CDCl3) δ 7.84 (d, J=8.2, 1H), 7.25 (d, J=8.2, 1H), 3.07 (t, J=6.2, 2H), 2.74 (t, J=6.7, 2H), 2.18-2.25 (m, 2H).