Reacción #77448

Ecuación de reacción

11-Benzyl-5-methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene

bromine

→

oil

Rendimiento 28.0%

11-BENZYL-6-BROMO-5-METHOXY-11-AZA-TRICYCLO[7.3.1.02,7]TRIDECA-2(7),3,5-TRIENE

Rendimiento 28.0%

Disolventes

CH2Cl2

CH2Cl2

AcOH

AcOH

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter 18 hours the reaction was quenched with 20% aq. NaHSO3 soln
2. 2
   ExtracciónThe product was extracted with CH2Cl2 (3×40 mL)
3. 3
   Lavadowashed with sat. aq. NaHCO3 soln
4. 4
   OtroThe combined organic layer was dried through a cotton plug
5. 5
   Concentraciónconcentrated
6. 6
   Otrochromatographed on Silica gel

Procedimiento

11-Benzyl-5-methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene (3.00 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 soln. (100 mL). The product was extracted with CH2Cl2 (3×40 mL) and washed with sat. aq. NaHCO3 soln. (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), 2.86-2.79 (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+).

Fuente