反应详情

温度

80 °C

Postassium bicarbonate (204 g, 2.04 mol) was suspended in CH3CN (12 L), and the mixture was heated to 80° C. Solutions of 1-bromo-2,3-bis(bromomethyl)benzene (280 g, 0.82 mol in 500 mL CH3CN) and benzylamine (87.5 g, 0.82 mol in 500 mL CH3CN) were added concurrently via addition funnels over 1 hour. The reaction mixture was then stirred at 77° C. for 16 hours. The contents of the reaction flask were cooled and filtered; the solvent was removed by evaporation; and the mixture was partitioned between 1M K2CO3 and EtOAc. The organic phases were washed with brine, dried with anhydrous Na2SO4, filtered, and evaporated. Flash column chromatography (gradient elution: heptane to 10% EtOAc in heptane) gave the title compound as a pale oil. 1H NMR (CDCl3) δ (ppm) 7.41-7.39 (m, 2H), 7.37-7.34 (m, 2H), 7.32-7.27 (m, 2H), 7.10-7.03 (m, 2H), 4.02 (s, 2H), 3.97 (s, 2H), 3.91 (s, 2H). LRMS (ESI) m/z 289 [(M+H)+; calcd for C15H15BrN: 289].

1. temperatureThe contents of the reaction flask were cooled
2. filtrationfiltered
3. customthe solvent was removed by evaporation
4. customand the mixture was partitioned between 1M K2CO3 and EtOAc
5. washThe organic phases were washed with brine
6. dry with materialdried with anhydrous Na2SO4
7. filtrationfiltered
8. customevaporated
9. washFlash column chromatography (gradient elution: heptane to 10% EtOAc in heptane)