5-Bromo-2-methoxythioanisole synthesis

Yield:66623-79-8 94%

Reaction Conditions:

with n-butyllithium in diethyl ether;hexane at -78; for 1.5 h;Inert atmosphere;

Steps:

1.1 (1) Synthesis of (5-bromo-2-methoxyphenyl)methylsulfane

2,4-dibromo-1-methoxybenzene (20 g, 75 mmol, a compound 1-1) is dissolved in dry diethyl ether (100 mL) under a nitrogen atmosphere, and 2.5 M n-BuLi (in hexane) (332 mL, 0.83 mol) is slowly added thereto in a dropwise fashion at -78° C. The mixture is stirred at the same temperature for 1 hour, and dimethyl disulfide (8.7 mL, 98 mmol) is slowly added thereto. After 30 minutes, an ammonium chloride saturated aqueous solution is added thereto to complete the reaction, and then diethyl ether is used to perform extraction. Then, an organic solvent layer obtained therefrom is dried with anhydrous MgSO₄, concentrated, and purified through silica gel column chromatography, obtaining a desired compound 1-2 (yield: 94%). ¹H NMR (300 MHz, CDCl₃) δ ppm 7.20-7.18 (m, 2H), 6.68 (d, J=8.4 Hz, 1H), 3.86 (s, 3H), 2.42 (s, 3H)

References:

US2016/226005,2016,A1 Location in patent:Paragraph 0104-0105