[CH2:1]([N:8]1[CH2:19][CH:18]2[CH2:20][CH:10]([CH2:11][C:12]3[CH:13]=[C:14]([O:21][CH3:22])[CH:15]=[CH:16][C:17]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:23]Br>C(Cl)Cl.CC(O)=O>[CH2:1]([N:8]1[CH2:19][CH:18]2[CH2:20][CH:10]([CH2:11][C:12]3[C:13]([Br:23])=[C:14]([O:21][CH3:22])[CH:15]=[CH:16][C:17]=32)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=111-Benzyl-5-methoxy-11-aza-tricyclo[7.3.1.02.7]trideca-2(7),3,5-triene (300 g, 10.2 mmol) was stirred at 0° C. in CH2Cl2 (10 mL) and AcOH (5 mL) and treated with bromine (3.21 g, 20 mmol) in CH2Cl2 (10 mL) and AcOH (5 mL). After 18 hours the reaction was quenched with 20% aq. NaHSO3 soin. (100 mL). The produce was extracted with CH2Cl2 (3×40 mL) and washed with sat. aq. NaHCO3 soin. (3×50 mL). The combined organic layer was dried through a cotton plug, concentrated and chromatographed on Silica gel to provide an oil (1.05 g, 28%). (TLC 30%EtOAc/hexanes Rf 0.48). 1H NMR (CDCl3) δ 7.13 (m, 3H), 6.91 (m, 3H), 6.68 (d, J=8.0 Hz, 1H), 3.90 (s, 3H), 3.36 (s, 2H), 2.88-2.79 (4H), 2.67 (br d, J=9.0 Hz, 1H), 2.31 (br s, 1H), 2.28 (br s, 1H), 2.22 (br s, 1H), 1.78 (AB d, J=13.0 Hz, 2H). GCMS m/e 373,371 (M+).
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