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ChemicalBook CAS DataBase List 2-bromo-1-methoxynaphthalene

2-bromo-1-methoxynaphthalene synthesis

3synthesis methods
-

Yield:62012-54-8 85.6%

Reaction Conditions:

with potassium hydroxide in acetonitrile at 40; for 12 h;

Steps:

4.3.1.2. 2-Bromo-1-methoxynaphthalene (16)
A solution of 15 (10 g,44.83 mmol), potassium hydroxide (5.03 g, 89.66 mmol), and methyliodide (16.74 mL, 268.98 mmol) in acetonitrile (80 mL) was stirred at40 °C for 12 h. The mixture was washed with water, extracted withdichloromethane, dried over anhydrous sodium sulfate andconcentrated in vacuo. The crude product was purified by silica gelcolumn eluting with petroleum ether: ethyl acetate (20/1) to give thedesired product (9.1 g, yield 85.6%) as a white solid. Rf=0.5 (1:6,ethyl acetate:petroleum ether). 1H NMR (400 MHz, CDCl3) δ 8.14 (d,J=7.2 Hz, 1H), 7.83 (d, J=7.2 Hz,1H), 7.59 - 7.49 (m, 4H), 4.01 (s,3H).

References:

He, Yulong;Dou, Huixia;Gao, Dingding;Wang, Ting;Zhang, Mingming;Wang, Heyao;Li, Yingxia [Bioorganic and Medicinal Chemistry,2019,vol. 27,# 19,art. no. 115015]

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