反应详情

A RBF was charged 2-methoxynaphthalene (2.00 g, 12.64 mmol) and THF (30 mL) to give a clear solution. n-butyllithium (2.5M in hexanes) (5.66 mL, 14.16 mmol) was added dropwise. The flask was cooled in a dry ice-acetone bath for 10 min and 1,2-dibromoethane (1.634 mL, 18.96 mmol) was added dropwise. The reaction was warmed to room temperature and stirred for 16 hours. NaOH (1 M, 10 mL, 10 mmol 0 was added and the reaction was heated to reflux for 1 hour. The mixture was cooled to room temperature and extracted with DCM (2×), and the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The crude solid was recrystallized from heptane to give 2-bromo-3-methoxynaphthalene (1.75 g, 7.38 mmol, 58.4% yield) as an off-white solid. m/z (ESI) 237.1 (M+H)+.

1. customto give a clear solution
2. temperatureThe flask was cooled in a dry ice-acetone bath for 10 min
3. temperaturethe reaction was heated
4. temperatureto reflux for 1 hour
5. temperatureThe mixture was cooled to room temperature
6. extractionextracted with DCM (2×)
7. dry with materialthe combined organic extracts were dried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude solid was recrystallized from heptane