Реакция #357321

Уравнение реакции

water

6-Bromo-2-naphthol

sodium hydride

ethyl iodide

→

solid

Выход 60.0%

2-Bromo-6-ethoxy-naphthalene

Выход 60.0%

Растворители

DMF

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe reaction was stirred overnight at rt
2. 2
   Экстракцияextracted several times with tert-butyl methyl ether
3. 3
   ПромывкаThe combined organic extracts were washed with water and brine
4. 4
   Сушкаdried over MgSO4
5. 5
   Фильтрацияfiltered
6. 6
   Другоеevaporated under reduced pressure
7. 7
   Другоеto give tan solid
8. 8
   ДругоеThis was recrystallized from MeOH
9. 9
   Другоеdried under high vacuum to a constant wt.

Методика

To a suspension of sodium hydride (800 mg, 60% oil dispersion) in DMF (20 ml) was added a solution of 6-Bromo-2-naphthol dropwise with stirring at 0°. After gas evolution had ceased, neat ethyl iodide (1.6 ml) was added dropwise to the stirred solution. The reaction was stirred overnight at rt. The reaction mixture was poured into water and extracted several times with tert-butyl methyl ether. The combined organic extracts were washed with water and brine, then dried over MgSO4, filtered and evaporated under reduced pressure to give tan solid. This was recrystallized from MeOH and dried under high vacuum to a constant wt. giving a white solid (3.11 g, 60%). 1H NMR(400 MHz, CDCl3) δ 7.92 (d, J=1.7 Hz, 1H), 7.65(d, J=8.9 Hz, 1H), 7.59 (d, J=8.7 Hz, 2H), 7.16 (dd, J=8.9 Hz, 2.48, 1H), 7.09 (d, J=2.4 Hz, 1H), 4.15 (q, 2H), 1.49 (t, 3H).

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